Ammonia → HCID 90102219, compound

HRID 1052783Notes

Reaction equation

[CH3:1][N:2]([CH3:53])[CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[C:23]3[C:22]([NH:24][C@H:25]([C:27]4[N:32]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:31](=[O:39])[C:30]5=[C:40]([CH3:43])[CH:41]=[CH:42][N:29]5[N:28]=4)[CH3:26])=[N:21][CH:20]=[N:19][C:18]=3[N:17](COCC[Si](C)(C)C)[CH:16]=2)[CH:12]=[C:11]([OH:52])[CH:10]=1)(=[O:7])=[O:6].FC(F)(F)C(O)=O.N>>[CH3:53][N:2]([CH3:1])[CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[C:23]3[C:22]([NH:24][C@H:25]([C:27]4[N:32]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:31](=[O:39])[C:30]5=[C:40]([CH3:43])[CH:41]=[CH:42][N:29]5[N:28]=4)[CH3:26])=[N:21][CH:20]=[N:19][C:18]=3[NH:17][CH:16]=2)[CH:12]=[C:11]([OH:52])[CH:10]=1)(=[O:6])=[O:7]

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736196(S)-2-(Dimethylamino)-N-(3-hydroxy-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)phenyl)ethanesulfonamide

Product 1

HCID 90102219HCID 90102219, compoundYield 52%

Procedure

(S)-2-(Dimethylamino)-N-(3-hydroxy-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)phenyl)ethanesulfonamide (15 mg, 0.02 mmol, 77% purity) was treated with trifluoroacetic acid (300 μl, 3.89 mmol) and a solution of ammonia (7N in methanol, 300 μl, 2.10 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 40% dichloromethane methanol) to obtain 5 mg (52% yield) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (0% to 40% dichloromethane methanol)

Sources & evidence

ORD record: ord-c55115187b3547949893764ba17a7a9d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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