Acetyl chloride → HCID 118272018, compound

HRID 590805Notes

Reaction equation

[NH2:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.CCN(C(C)C)C(C)C.[C:51](Cl)(=[O:53])[CH3:52]>C1COCC1>[C:17]1([C@H:15]([NH:14][C:12](=[O:13])[NH:11][C:9]2[N:8]=[CH:7][C:6]3[C:2]([NH:1][C:51](=[O:53])[CH3:52])=[N:3][N:4]([C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:5]=3[CH:10]=2)[CH3:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (900 mg, 1.671 mmol) and DIEA (0.584 mL, 3.34 mmol) in THF (16 mL) at 0° C. was treated drop-wise with a solution of acetyl chloride (0.131 mL, 1.838 mmol) in THF (0.5 mL). The reaction was stirred at 0° C. for 10 min, then allowed to warm to room temperature and stirred for 1 h. The solvent was evaporated in vacuo and purified by flash chromatography (0-30% EtOAc/DCM) to afford (R)—N-(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. MS ESI calc'd. For C36H32N6O2 [M+1]+ 581. found 581.

Workup

temperatureto warm to room temperature
stirringstirred for 1 h
customThe solvent was evaporated in vacuo
custompurified by flash chromatography (0-30% EtOAc/DCM)

Sources & evidence

ORD record: ord-b751cf5104f04063b0fa041e8cdb42e7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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