Ammonia → (S)-N-(3-Hydroxy-5-(3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1H-pyrazol-1-yl)phenyl)methanesulfonamide

HRID 1052741Notes

Reaction equation

HRID 1052741 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:6]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([C:14]3[C:22]4[C:21]([NH:23][C@H:24]([C:26]5[N:31]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)[C:30](=[O:38])[C:29]6=[C:39]([CH3:42])[CH:40]=[CH:41][N:28]6[N:27]=5)[CH3:25])=[N:20][CH:19]=[N:18][C:17]=4[N:16](COCC[Si](C)(C)C)[CH:15]=3)=[N:10]2)[CH:8]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([NH:51][S:52]([CH3:55])(=[O:53])=[O:54])[CH:6]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([C:14]3[C:22]4[C:21]([NH:23][C@H:24]([C:26]5[N:31]([C:32]6[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=6)[C:30](=[O:38])[C:29]6=[C:39]([CH3:42])[CH:40]=[CH:41][N:28]6[N:27]=5)[CH3:25])=[N:20][CH:19]=[N:18][C:17]=4[NH:16][CH:15]=3)=[N:10]2)[CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736247(S)-N-(3-Methoxy-5-(3-(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)-1H-pyrazol-1-yl)phenyl)methanesulfonamide

Product 1

HCID 136266527(S)-N-(3-Hydroxy-5-(3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1H-pyrazol-1-yl)phenyl)methanesulfonamideYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-Methoxy-5-(3-(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)-1H-pyrazol-1-yl)phenyl)methanesulfonamide (15 mg, 0.01 mmol) was treated with boron tribromide (1M in dichloromethane, 1 ml, 1 mmol) in dichloromethane (1 ml) and then with a solution of ammonia (7N in methanol, 10 ml, 70 mmol) according to the method described in Example 41 to give 4.2 mg (44% yield) of the title compound. Purity 92%.

Sources & evidence

ORD record
ord-5ef8ed12e257482c86032f3f8555313d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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