Water → HCID 118272112, compound

HRID 588165Notes

Reaction equation

HRID 588165 reaction equation
Cl[CH2:2][C:3]1[C:8]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:6]=[C:5]([NH:33][C:34]([NH:36][C@H:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:38])=[O:35])[N:4]=1.[H-].[Na+].CC[O:49]C(C)=O.O.[CH2:54]1C[O:57][CH2:56][CH2:55]1>>[OH:49][CH:55]([CH3:54])[CH2:56][O:57][CH2:2][C:3]1[C:8]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:6]=[C:5]([NH:33][C:34]([NH:36][C@H:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:38])=[O:35])[N:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 118272000HCID 118272000, compound2×

Product 1

HCID 118272112HCID 118272112, compoundYield 100%

Procedure

To the solution of (S)-1-(4-(chloromethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (50 mg, 0.083 mmol) in THF (1.0 ml) was added sodium hydride (4.98 mg, 0.125 mmol). The resulting reaction mixture was allowed to stir at rt for 10 min before (S)-1-(4-(chloromethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (50 mg, 0.083 mmol) was added into the above solution. The reaction solution was stirred for 2 h at rt. EtOAc and water was added into the mixture and the organic layer was collected and washed by water and brine. After drying over Na2SO4, the solution was concentrated to give 1-(4-((2-hydroxypropoxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-((S)-1-phenylethyl)urea (53.3 mg, 0.083 mmol, 100% yield) without purification. MS: [M+H]+ m/z 642.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added into the above solution
  3. customthe organic layer was collected
  4. washwashed by water and brine
  5. dry with materialAfter drying over Na2SO4
  6. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-61facdb3c9a54d74bb886e2c5391cea5
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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