Ammonia → HCID 118433723, compound

HRID 1052825Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:6]=[C:7]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[N:11](COCC[Si](C)(C)C)[CH:10]=2)[CH:8]=1)#[N:2].FC(F)(F)C(O)=O.N>>[C:1]([C:3]1[CH:4]=[C:5]([NH:46][S:47]([CH3:50])(=[O:48])=[O:49])[CH:6]=[C:7]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)[CH:8]=1)#[N:2]

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736170HCID 131736170, compound

Product 1

HCID 118433723HCID 118433723, compoundYield 67.3%

Procedure

(S)—N-(3-Cyano-5-(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)phenyl)methanesulfonamide (145 mg, 0.20 mmol) was treated with trifluoroacetic acid (3.8 ml, 49 mmol) and a solution of ammonia (7N in methanol, 3.8 ml, 27 mmol) according to the method described in Example 27 to give 78 mg (66% yield) of the title compound. Purity 100%.

Sources & evidence

ORD record: ord-36b5c186f6404ec1ae6b60b64309d9a8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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