Ammonia → HCID 73776363, compound

HRID 1052695Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[C:18]2[C:17]([NH:19][C@H:20]([C:22]3[N:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26](=[O:34])[C:25]4=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]4[N:23]=3)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=2[N:12](COCC[Si](C)(C)C)[CH:11]=1.B(Br)(Br)Br.N>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:10]1[C:18]2[C:17]([NH:19][C@H:20]([C:22]3[N:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26](=[O:34])[C:25]4=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]4[N:23]=3)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=2[NH:12][CH:11]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 25134Boron tribromide

HCID 131736138HCID 131736138, compound

Product 1

HCID 73776363HCID 73776363, compoundYield 36%

Procedure

2-((1S)-1-((5-(2-Fluoro-6-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.07 mmol) was treated with boron tribromide (1M in dichloromethane, 680 μl, 0.68 mmol) and a solution of ammonia (7N in methanol, 1 mL, 7 mmol) according to the method described in Example 41 to give 12 mg (36% yield) of the title compound as a white solid. Purity 97%.

Sources & evidence

ORD record: ord-800ccae526494b0c9b36de4fc355d17e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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