Tetrahydrofuran → HCID 57758058, compound

HRID 229622Notes

Reaction equation

HRID 229622 reaction equation
C1COCC1.[NH2:6][C:7]1[C:12]2=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=4[F:40])=[O:28])=[CH:22][CH:21]=3)[C:14]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CCOC(C)=O>[NH2:6][C:7]1[C:12]2=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[CH:32][C:31]=4[F:40])=[O:28])=[CH:22][CH:21]=3)[C:14]([CH2:16][CH2:17][CH:18]=[O:19])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 159087TriacetoxyperiodinaneHCID 57758345HCID 57758345, compound

Product 1

HCID 57758058HCID 57758058, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of THF (5 mL) was added N-{4-[4-amino-6-(3-hydroxypropyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]phenyl}-N′-[2-fluoro-5-(trifluoromethyl)phenyl]urea (55 mg, 0.11 mmol) followed by Dess-Martin Periodinane reagent (0.29 mL, 0.14 mmol, 15% wt in CH2Cl2). The reaction was stirred until HPLC indicated completion of reaction (2 h). The reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3/Na2S2O3 1:1 (3×). The aqueous layer was back extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4), filtered, and evaporated to give a crude yellow solid (53 mg, 96%) that was used without further purification. 1H-NMR (DMSO-d6) δ 9.35 (s, 1H), 8.98 (s, 1H), 8.62 (d, J=7.2 Hz, 1H), 7.80 (s, 1H), 7.62 to 7.28 (m, 6H), 2.71 (t, J=7.5 Hz, 2H), 2.41 (t, J=7.4 Hz, 2H); MS [M+H]+=487; LCMS RT=2.62 min.

Workup

  1. customcompletion of reaction (2 h)
  2. washwashed with saturated aqueous NaHCO3/Na2S2O3 1:1 (3×)
  3. extractionThe aqueous layer was back extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e1c7ae86ffc54e77bf86d6a2976e2bca
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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