Ammonia → HCID 118433862, compound

HRID 1052849Notes

Reaction equation

[CH3:1][N:2]([CH3:53])[C:3](=[O:52])[C:4]1[CH:9]=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:7]=[C:6]([C:15]2[C:23]3[C:22]([NH:24][C@H:25]([C:27]4[N:32]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:31](=[O:39])[C:30]5=[C:40]([CH3:43])[CH:41]=[CH:42][N:29]5[N:28]=4)[CH3:26])=[N:21][CH:20]=[N:19][C:18]=3[N:17](COCC[Si](C)(C)C)[CH:16]=2)[CH:5]=1.FC(F)(F)C(O)=O.N>>[CH3:53][N:2]([CH3:1])[C:3](=[O:52])[C:4]1[CH:9]=[C:8]([NH:10][S:11]([CH3:14])(=[O:12])=[O:13])[CH:7]=[C:6]([C:15]2[C:23]3[C:22]([NH:24][C@H:25]([C:27]4[N:32]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:31](=[O:39])[C:30]5=[C:40]([CH3:43])[CH:41]=[CH:42][N:29]5[N:28]=4)[CH3:26])=[N:21][CH:20]=[N:19][C:18]=3[NH:17][CH:16]=2)[CH:5]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736178(S)-N,N-Dimethyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrol o[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)benzamide

Product 1

HCID 118433862HCID 118433862, compoundYield 82.2%

Procedure

(S)—N,N-Dimethyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)benzamide (215 mg, 0.28 mmol) was treated with trifluoroacetic acid (3.0 ml, 39 mmol) and a solution of ammonia (7N in methanol, 3.0 ml, 21 mmol) according to the method described in Example 27 to give 144 mg (81% yield) of the title compound. Purity 99%.

Sources & evidence

ORD record: ord-379316ce5583447b9467dfe7bd2d4117
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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