Ammonia → HCID 73775933, compound

HRID 1052725Notes

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][CH:33]=[C:32]([S:36]([N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)(=[O:38])=[O:37])[CH:31]=4)=[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:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([S:36]([N:39]5[CH2:40][CH2:41][O:42][CH2:43][CH2:44]5)(=[O:37])=[O:38])[CH:31]=4)=[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 131736215HCID 131736215, compound

Product 1

HCID 73775933HCID 73775933, compoundYield 25.9%

Procedure

(S)-5-Methyl-2-(1-((5-(3-(morpholinosulfonyl)phenyl)-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 (90 mg, 0.12 mmol) was treated with trifluoroacetic acid (2 ml, 25 mmol) and a solution of ammonia (7N in methanol, 2 ml, 91 mmol) according to the method described in Example 27. The residue was purified by reverse phase using SP1® Purification System to obtain 19 mg (25% yield) of the title compound. Purity 98%.

Workup

customThe residue was purified by reverse phase
custom® Purification System

Sources & evidence

ORD record: ord-d88457b17e944cd4a150d3acddef558a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

Loading…