Ammonia → HCID 136992752, compound

HRID 1052800Notes

Reaction equation

HRID 1052800 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:24]([NH:26][C@H:27]([C:29]5[N:34]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:33](=[O:41])[C:32]6=[C:42]([CH3:45])[CH:43]=[CH:44][N:31]6[N:30]=5)[CH3:28])=[N:23][CH:22]=[N:21][C:20]=4[N:19](COCC[Si](C)(C)C)[CH:18]=3)=[N:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH:16]=[CH:15][C:14]([C:17]3[C:25]4[C:24]([NH:26][C@H:27]([C:29]5[N:34]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:33](=[O:41])[C:32]6=[C:42]([CH3:45])[CH:43]=[CH:44][N:31]6[N:30]=5)[CH3:28])=[N:23][CH:22]=[N:21][C:20]=4[NH:19][CH:18]=3)=[N:13]2)(=[O:10])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736269HCID 131736269, compound

Product 1

HCID 136992752HCID 136992752, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((5-(1-((3-Methoxyphenyl)sulfonyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (48.5 mg, 0.06 mmol) was treated with boron tribromide (1M in dichloromethane, 0.75 ml, 0.75 mmol) in dichloromethane (2 ml) and then with a solution of ammonia (7N in methanol, 5 ml, 35 mmol) according to the method described in Example 41 to give 6.7 mg (17% yield) of the title compound. Purity 98%.

Sources & evidence

ORD record
ord-298cf490f1cf47859f98b9287a4c1496
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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