Ammonia → HCID 90103190, compound

HRID 1052856Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]5[N:36]([S:39]([CH3:42])(=[O:41])=[O:40])[CH:37]=[CH:38][C:31]=45)=[CH:28][N:27](COCC[Si](C)(C)C)[C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.FC(F)(F)C(O)=O.N>>[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]5[N:36]([S:39]([CH3:42])(=[O:41])=[O:40])[CH:37]=[CH:38][C:31]=45)=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736223HCID 131736223, compound

Product 1

HCID 90103190HCID 90103190, compoundYield 94.9%

Procedure

(S)-5-Methyl-2-(1-((5-(1-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (30 mg, 0.04 mmol) was treated with trifluoroacetic acid (1 ml, 13 mmol) and a solution of ammonia (7N in methanol, 1 ml, 60 mmol) according to the method described in Example 27 to give 22 mg (88% yield) of the title compound as a white solid. Purity 98%.

Sources & evidence

ORD record: ord-a5e56b3fc83b472089491d1cc11f585d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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