Methanesulfonyl chloride → (S)-N-(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)thio)phenyl)methanesulfonamide

HRID 1052598Notes

Reaction equation

HRID 1052598 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[CH:10]=2)=[CH:4][CH:3]=1.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>>[CH3:37][C:34]1[CH:35]=[CH:36][N:23]2[C:24]=1[C:25](=[O:33])[N:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]([C@@H:19]([NH:18][C:16]1[C:17]3[C:9]([S:8][C:5]4[CH:6]=[CH:7][C:2]([NH:1][S:47]([CH3:46])(=[O:49])=[O:48])=[CH:3][CH:4]=4)=[CH:10][N:11]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:45])[CH3:44])[C:12]=3[N:13]=[CH:14][N:15]=1)[CH3:20])=[N:22]2

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131736221(S)-2-(1-((5-((4-Aminophenyl)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

Product 1

HCID 131736222(S)-N-(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)thio)phenyl)methanesulfonamide

Procedure

(S)-2-(1-((5-((4-Aminophenyl)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 (50 mg, 0.08 mmol) was treated with methanesulfonyl chloride (10 μl, 0.14 mmol) according to the method described in Preparation 15b. The residue (15 mg, 85% purity) was used in the next synthetic step without further purification.

Workup

  1. customThe residue (15 mg, 85% purity) was used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-ecb62ded90ce4dd2b7061260f15d579c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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