Ammonia → HCID 73776211, compound

HRID 1052699Notes

Reaction equation

HRID 1052699 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:45]C)=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[N:10](COCC[Si](C)(C)C)[CH:9]=2)[CH:7]=1.B(Br)(Br)Br.N>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:45])=[C:6]([C:8]2[C:16]3[C:15]([NH:17][C@H:18]([C:20]4[N:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:24](=[O:32])[C:23]5=[C:33]([CH3:36])[CH:34]=[CH:35][N:22]5[N:21]=4)[CH3:19])=[N:14][CH:13]=[N:12][C:11]=3[NH:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736144HCID 131736144, compound

Product 1

HCID 73776211HCID 73776211, compoundYield 47%

Procedure

(S)-2-(1-((5-(5-Fluoro-2-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 (55 mg, 0.09 mmol) was treated with boron tribromide (1 M in dichloromethane, 1 mL, 1 mmol) and a solution of ammonia (7N in methanol, 1 mL, 7 mmol) according to the method described in Example 27 to give 20 mg (47% yield) of the title. Purity 94%.

Workup

  1. customto give 20 mg (47% yield) of the title

Sources & evidence

ORD record
ord-ed9a713abf034feda0fddeb2912151ad
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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