Ammonia → HCID 73775415, compound

HRID 1052706Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736147HCID 131736147, compound

Product 1

HCID 73775415HCID 73775415, compoundYield 11.4%

Procedure

(S)-2-(1-((5-(1H-Indol-7-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 (91 mg, 0.14 mmol) was treated with trifluoroacetic acid (1.82 mL, 23.62 mmol) and a solution of ammonia (7N in methanol, 1.82 mL, 12.74 mmol) according to the method described in Example 27 to give 8 mg (11% yield) of the title compound. Purity 98%.

Sources & evidence

ORD record: ord-17f074d0601f4555813d53c85843da87
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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