Ammonia → HCID 73776071, compound

HRID 1052734Notes

Reaction equation

HRID 1052734 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[C:18]2[C:17]([NH:19][C@H:20]([C:22]3[N:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26](=[O:34])[C:25]4=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]4[N:23]=3)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=2[N:12](COCC[Si](C)(C)C)[CH:11]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[C:18]2[C:17]([NH:19][C@H:20]([C:22]3[N:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26](=[O:34])[C:25]4=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]4[N:23]=3)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=2[NH:12][CH:11]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736252HCID 131736252, compound

Product 1

HCID 73776071HCID 73776071, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((5-((2-Methoxyphenyl)thio)-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 (57 mg, 0.09 mmol) was treated with boron tribromide (1M in dichloromethane, 872 μL, 0.87 mmol) in dichloromethane (1.14 mL) and then with a solution of ammonia (7N in methanol, 1.14 ml, 7.98 mmol) according to the method described in Example 27. The residue was purified using SP1® Purification System (0% to 100% dichloromethane ethyl acetate) to obtain 23 mg (47% yield, 90% purity) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 100% dichloromethane ethyl acetate)

Sources & evidence

ORD record
ord-7deca952ab5f48da9c34dff582a27d39
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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