Acetic Anhydride → HCID 118131309, compound

HRID 634464Notes

Reaction equation

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 118131359HCID 118131359, compound

Product 1

HCID 118131309HCID 118131309, compoundYield 10%

Procedure

3-(1-(4-amino-3-(2-aminothiazol-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one hydrochloride (Example 59, 23 mg, 0.044 mmol) was dissolved in TEA (124 μL, 0.888 mmol)/Ac2O (419 μL, 4.44 mmol) and stirred at rt for 1 h. The reaction mixture was quenched by the addition of 1M HCl (1 ml) and purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile to give the title compound (2.3 mg, 9.9%) as yellowish solid.

Workup

customThe reaction mixture was quenched by the addition of 1M HCl (1 ml)
custompurified via reverse phase chromatography

Sources & evidence

ORD record: ord-67fc72130d0d4b10bd517c9cd41ebcf1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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