Tetrahydrofuran → HCID 57526831, compound

HRID 1452635Notes

Reaction equation

HRID 1452635 reaction equation
O1CCCC1.[C:6]([O:10][C:11]([N:13]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=1)[C:14]1[N:19]2[N:20]=[CH:21][CH:22]=[C:18]2[N:17]=[C:16](Cl)[C:15]=1[CH2:24][C:25]([NH:27][C@H:28]1[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]1)=[O:26])=[O:12])([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[C:6]([O:10][C:11]([N:13]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=1)[C:14]1[N:19]2[C:18](=[CH:22][CH:21]=[N:20]2)[N:17]=[C:16]2[C:15]=1[CH2:24][C:25](=[O:26])[N:27]2[C@H:28]1[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86613786HCID 86613786, compound

Product 1

HCID 57526831HCID 57526831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of tetrahydrofuran (0.3 mL) and N,N-dimethylformamide (0.1 mL) containing tert-butyl (S)-3-(2-{7-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]-5-chloropyrazolo[1,5-a]pyrimidin-6-yl}acetylamino)piperidine-1-carboxylate (4.3 mg), sodium hydride (with 40% mineral oil added) (10 mg) was added, and the mixture was stirred at room temperature for 1 hr. To the reaction solution, aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off to obtain the title compound.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. filtrationAfter the sodium sulfate was filtered off
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2da3134679b14ac4bc90560068dfefff
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

Loading…