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Thionyl Chloride → HCID 57494727, compound

HRID 861164
Notes
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Reaction equation

HRID 861164 reaction equation
S(Cl)(Cl)=O.[CH2:5]1[S:9][C@@H:8]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C@H:7]2[NH:17][C:18]([NH:20][C@@H:6]12)=[O:19].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:41]([C:42]3[CH:47]=[CH:46][N:45]=[C:44]([NH:48][CH2:49][CH2:50][CH2:51][CH3:52])[N:43]=3)=[C:31]3[CH:32]=[CH:33][CH:34]=[C:35]([NH:36][CH2:37][CH2:38][CH2:39][CH3:40])[N:30]3[N:29]=2)=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[O:19]=[C:18]1[NH:20][C@H:6]2[CH2:5][S:9][C@@H:8]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]4[C:41]([C:42]5[CH:47]=[CH:46][N:45]=[C:44]([NH:48][CH2:49][CH2:50][CH2:51][CH3:52])[N:43]=5)=[C:31]5[CH:32]=[CH:33][CH:34]=[C:35]([NH:36][CH2:37][CH2:38][CH2:39][CH3:40])[N:30]5[N:29]=4)=[CH:26][CH:27]=3)=[O:16])[C@H:7]2[NH:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 171548BiotinHCID 516892Sodium BicarbonateHCID 10113479N-{4-[2-(4-aminophenyl)-7-(butylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-butylamine

Product 1

HCID 57494727HCID 57494727, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) solution of thionyl chloride (1 mL) was added solid d-(+)-biotin (100 mg, 0.41 mmol). The resulting mixture was warmed to room temperature and stirred for 1 hour. The excess thionyl chloride and other volatiles were removed under vacuum (<0.1 mm Hg) resulting in a solid residue. To this residue at 0° C. was added N,N-dimethylformamide (3 mL) followed by 2-(4-aminophenyl)-N-butyl-3-[2-(butylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-7-amine (70 mg, 0.16 mmol) in 2 mL of N,N-dimethylformamide. The resultant solution was stirred at room temperature for 1 hour at which time the reaction appeared to be complete by analytical methods. The solution was stirred an additional 72 hours. Ethyl acetate and saturated aqueous sodium bicarbonate were added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over sodium sulfate. Filtration and concentration followed by flash chromatography (8% methanol in dichloromethane) provided 5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-N-(4-{7-(butylamino)-3-[2-(butylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)pentanamide (30 mg, 28%) as a yellow solid. 1H NMR (DMSO-d6): δ 10.00 (s, 1 H), 7.90 (d, 1 H), 7.66 (m, 3 H), 7.46 (d, 2 H), 7.29 (t, 1 H), 6.99–6.94 (m, 2 H), 6.40 (s, 1 H), 6.32 (s, 1 H), 6.11–6.09 (m, 2 H), 6.25 (m, 1 H), 4.09 (m, 1 H), 3.47–3.06 (m, 4 H), 2.77 (m, 1 H), 2.53 (m, 1 H), 2.44 (m, 1 H), 2.97 (m, 2 H), 1.62–1.27 (m, 14 H), 0.89–0.83 (m, 6 H); MS m/z 656 (M+1).

Workup

  1. customThe excess thionyl chloride and other volatiles were removed under vacuum (<0.1 mm Hg)
  2. customresulting in a solid residue
  3. stirringThe solution was stirred an additional 72 hours
  4. customthe layers separated
  5. washThe organic layer was washed with brine
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. dry with materialthe combined organics were dried over sodium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-aabb4a03b0fa40c795d0b012de845e7f
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153855B2

Reaction notes

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