Ammonia → HCID 73775412, compound

HRID 1052719Notes

Reaction equation

HRID 1052719 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([O:46]C)[CH:45]=1)[CH2:5][C:6]1[C:14]2[C:13]([NH:15][C@H:16]([C:18]3[N:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:22](=[O:30])[C:21]4=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]4[N:19]=3)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=2[N:8](COCC[Si](C)(C)C)[CH:7]=1.B(Br)(Br)Br.N>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([OH:46])[CH:45]=1)[CH2:5][C:6]1[C:14]2[C:13]([NH:15][C@H:16]([C:18]3[N:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:22](=[O:30])[C:21]4=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]4[N:19]=3)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=2[NH:8][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736179HCID 131736179, compound

Product 1

HCID 73775412HCID 73775412, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((5-(3-Fluoro-5-methoxybenzyl)-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 (3 mg, 0.01 mmol) was treated with boron tribromide (1M in dichloromethane, 148 μL, 0.15 mmol) in dichloromethane (280 μL) and then with a solution of ammonia (7N in methanol, 280 μl, 1.96 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (0% to 100% dichloromethane-ethyl acetate) to obtain 3 mg (38% yield) 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-8a87abbb445c4ad29451e284b7117eec
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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