Acetyl chloride → N-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)acetamide

HRID 588147Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]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:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[C:42](Cl)(=[O:44])[CH3:43].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:42](=[O:44])[CH3:43])[C:5]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-amine (115 mg, 0.261 mmol) was taken up in THF (2.6 ml) and cooled to 0° C. DIPEA (228 μl, 1.304 mmol) followed by acetyl chloride (93 μl, 1.304 mmol) was added. The mixture was allowed to stir, reaching room temperature overnight. EtOAc and saturated NH4Cl were added. The products were extracted into EtOAc (3×). The combined organic layers were washed with brine, dried over Mg SO4, and concentrated in vacuo to give N-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)acetamide (48B). Reaction products were carrried forward without purification. MS: [M+H]+ m/z 483.

Workup

additionwas added
extractionThe products were extracted into EtOAc (3×)
washThe combined organic layers were washed with brine
dry with materialdried over Mg SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c31fb4da8f734a94b1576d5f398fa6b0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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