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Pyridine → HCID 86268825, compound

HRID 2279008
Notes
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Reaction equation

HRID 2279008 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][CH2:7][C@H:8]([N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15])[CH3:9].N1C=CC=CC=1.[CH3:22][N:23]1[CH:27]=[C:26]([C:28]2[CH:33]=[C:32]([O:34][C:35]3[CH:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=3)[CH:31]=[CH:30][N:29]=2)[CH:25]=[N:24]1>C(Cl)Cl.CCOC(C)=O>[CH3:5][O:6][CH2:7][C@H:8]([N:10]1[CH2:14][CH2:13][N:12]([C:11]([NH:41][C:38]2[CH:37]=[CH:36][C:35]([O:34][C:32]3[CH:31]=[CH:30][N:29]=[C:28]([C:26]4[CH:25]=[N:24][N:23]([CH3:22])[CH:27]=4)[CH:33]=3)=[CH:40][N:39]=2)=[O:15])[C:1]1=[O:2])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 593227775-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-2-amineHCID 90426016HCID 90426016, compound

Product 1

HCID 86268825HCID 86268825, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

Phosgene (15% in toluene, 1.75 mL, 2.449 mmol) was treated with a solution of (R)-1-(1-methoxypropan-2-yl)imidazolidin-2-one (155 mg, 0.980 mmol) and pyridine (116 mg, 1.470 mmol) in DCM (2 mL), stirred at RT for 15 min, then concentrated to dryness. The residue was dissolved in DCM (2 mL), treated with a solution of Example A2 (131 mg, 0.490 mmol) and TEA (248 mg, 2.449 mmol) in DCM (2 mL) and stirred at RT for 4 h. The mixture was treated with EtOAc, washed with satd. NaHCO3, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford (R)-3-(1-methoxypropan-2-yl)-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (38 mg, 17%). 1H NMR (400 MHz, DMSO-d6): δ 10.98 (s, 1 H), 8.37 (d, J=5.7 Hz, 1 H), 8.25 (s, 1 H), 8.22-8.21 (m, 1 H), 8.06-8.05 (m, 1 H), 7.95 (d, J=0.7 Hz, 1 H), 7.72 (dd, J=9.0, 2.9 Hz, 1 H), 7.22 (d, J=2.4 Hz, 1 H), 6.69 (dd, J=5.7, 2.4 Hz, 1 H), 4.10-4.09 (m, 1 H), 3.84 (s, 3 H), 3.81-3.79 (m, 2 H), 3.40-3.39 (m, 4 H), 3.26 (s, 3 H), 1.09 (d, J=6.9 Hz, 3H); MS (ESI) m/z: 452.2 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in DCM (2 mL)
  3. stirringstirred at RT for 4 h
  4. washwashed with satd
  5. dry with materialNaHCO3, then brine, dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-99bd65751a10424999512ccce4d4cc51
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133183B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes