Ammonia → HCID 90102949, compound

HRID 1052803Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736164(S)-N-(4-Hydroxy-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)phenyl)methanesulfonamide

Product 1

HCID 90102949HCID 90102949, compoundYield 30.4%

Procedure

(S)—N-(4-Hydroxy-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)phenyl)methanesulfonamide (102 mg, 0.15 mmol) was treated with trifluoroacetic acid (2.7 ml, 35.05 mmol) and a solution of ammonia (7N in methanol, 2.7 ml, 19 mmol) according to the method described in Example 27 to give 26 mg (29% yield) of the title compound. Purity 93%.

Sources & evidence

ORD record: ord-2e54b295425f4f5994db345e7d764d63
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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