Ammonia → HCID 90103103, compound

HRID 1052811Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736271(S)-3-Hydroxy-N,N-dimethyl-5-(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)benzamide

Product 1

HCID 90103103HCID 90103103, compoundYield 85%

Procedure

(S)-3-Hydroxy-N,N-dimethyl-5-(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)benzamide (44 mg, 0.06 mmol, 89% purity) was treated with trifluoroacetic acid (880 μl, 11.42 mmol) and a solution of ammonia (7N in methanol, 880 μl, 6.16 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 15% dichloromethane-2-propanol) to obtain 27 mg (85% yield) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (0% to 15% dichloromethane-2-propanol)

Sources & evidence

ORD record: ord-80e841026bec47938af1343db1d8b6be
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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