Ammonia → HCID 90102159, compound

HRID 1052834Notes

Reaction equation

HRID 1052834 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:6]=[CH:7][C:8]=1[C:9]1[C:17]2[C:16]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=2[N:11](COCC[Si](C)(C)C)[CH:10]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([NH:46][S:47]([CH3:50])(=[O:48])=[O:49])[CH:6]=[CH:7][C:8]=1[C:9]1[C:17]2[C:16]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=2[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736172(S)-N-(3-Methoxy-4-(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)methanesulfonamide

Product 1

HCID 90102159HCID 90102159, compoundYield 464.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(3-Methoxy-4-(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)methanesulfonamide (159 mg, 0.02 mmol) was treated with boron tribromide (1M in dichloromethane, 0.61 ml, 0.61 mmol) in dichloromethane (1 ml) as a solvent and then with a solution of ammonia (7N in methanol, 4 ml, 28 mmol) according to the method described in Example 41 to give 53 mg (46% yield) of the title compound. Purity 100%.

Sources & evidence

ORD record
ord-fbd299c5e06149768d47dbd56125ec35
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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