Thionyl Chloride → (R)-1-(4-(chloromethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 588164Notes

Reaction equation

O[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.S(Cl)([Cl:47])=O>C(Cl)Cl>[Cl:47][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

Conditions

Temperature: 50 °C

Procedure

A solution of (R)-1-(4-(hydroxymethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (800 mg, 1.371 mmol, see Example 109) and thionyl chloride (0.110 ml, 1.508 mmol) in DCM (15 ml) was allowed to stir at 50° C. for 18 h. Removed the solvent by reduced pressure and the residue was purified on silical gel 0-100% EtOAc/Hexane and yielded (R)-1-(4-(chloromethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (402 mg, 0.668 mmol, 49% yield). MS: [M+H]+ m/z 602.

Workup

customRemoved the solvent by reduced pressure
customthe residue was purified on silical gel 0-100% EtOAc/Hexane

Sources & evidence

ORD record: ord-81f302ad716d4862a88f874472d973b0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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