Water → HCID 57526792, compound

HRID 1452634Notes

Reaction equation

HRID 1452634 reaction equation
O1[CH2:5][CH2:4][CH2:3]C1.[CH3:6]N(C)C=O.C(O[C:16]([N:18]([C:49]1[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH3:57])=[CH:51][CH:50]=1)[C:19]1[N:24]2[N:25]=[CH:26][CH:27]=[C:23]2[N:22]=[C:21]([NH:28][C@H:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]2)[C:20]=1[CH2:42][CH2:43]OS(C)(=O)=O)=[O:17])(C)(C)C.[H-].[Na+].[OH2:60]>>[C:4]([O:60][C:16]([N:18]([C:49]1[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH3:57])=[CH:51][CH:50]=1)[C:19]1[N:24]2[C:23](=[CH:27][CH:26]=[N:25]2)[N:22]=[C:21]2[C:20]=1[CH2:42][CH2:43][N:28]2[C@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[CH2:30]1)=[O:17])([CH3:3])([CH3:5])[CH3:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 57526822HCID 57526822, compound

Product 1

HCID 57526792HCID 57526792, compound

Procedure

To a mixed solution of tetrahydrofuran (3 mL) and N,N-dimethylformamide (1 mL) containing tert-butyl (S)-3-[7-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]-6-(2-methanesulfonyloxyethyl)pyrazolo[1,5-a]pyrimidin-5-ylamino]piperidine-1-carboxylate (0.693 mmol), sodium hydride (with 40% mineral oil added) (55 mg) was added with ice-cooling, and the mixture was stirred for 2 hr. After the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and 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 with ice-
  2. temperaturecooling
  3. additionwas added to the reaction solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter the sodium sulfate was filtered off
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6349ac6e3c78431281311df8399b4eba
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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