Ammonia → HCID 90102230, compound

HRID 1052776Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[C:25]3[C:24]([NH:26][C@H:27]([C:29]4[N:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:33](=[O:41])[C:32]5=[C:42]([CH3:45])[CH:43]=[CH:44][N:31]5[N:30]=4)[CH3:28])=[N:23][CH:22]=[N:21][C:20]=3[N:19](COCC[Si](C)(C)C)[CH:18]=2)[CH:14]=[N:13]1)(C(C)(C)C)(C)C.FC(F)(F)C(O)=O.N>>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[C:25]3[C:24]([NH:26][C@H:27]([C:29]4[N:34]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[C:33](=[O:41])[C:32]5=[C:42]([CH3:45])[CH:43]=[CH:44][N:31]5[N:30]=4)[CH3:28])=[N:23][CH:22]=[N:21][C:20]=3[NH:19][CH:18]=2)[CH:14]=[N:13]1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736212HCID 131736212, compound

Product 1

HCID 90102230HCID 90102230, compoundYield 68%

Procedure

(S)-2-(1-((5-(1-(3-((tert-Butyldimethylsilyl)oxy)propyl)-1H-pyrazol-4-yl)-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 (124 mg, 0.14 mmol) was treated with trifluoroacetic acid (1 ml, 13 mmol) and a solution of ammonia (7N in methanol, 2 ml, 14 mmol) according to the method described in Example 27 to give 48 mg (68% yield) of the title compound. Purity 99%.

Sources & evidence

ORD record: ord-ad9541796a2a46828edd9145c3a6b11a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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