Sodium Carbonate → (S)-N,N-Dimethyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrol o[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)benzamide

HRID 1052517Notes

Reaction equation

HRID 1052517 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=1.[CH3:39][N:40]([CH3:63])[C:41](=[O:62])[C:42]1[CH:47]=[C:46](B2OC(C)(C)C(C)(C)O2)[CH:45]=[C:44]([NH:57][S:58]([CH3:61])(=[O:60])=[O:59])[CH:43]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:39][N:40]([CH3:63])[C:41](=[O:62])[C:42]1[CH:43]=[C:44]([NH:57][S:58]([CH3:61])(=[O:60])=[O:59])[CH:45]=[C:46]([C:2]2[C:10]3[C:9]([NH:11][C@H:12]([C:14]4[N:19]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:18](=[O:26])[C:17]5=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]5[N:15]=4)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=2)[CH:47]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 90102811HCID 90102811, compoundHCID 131736122(S)-2-(1-((5-Bromo-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 131736178(S)-N,N-Dimethyl-3-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrol o[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-5-(methylsulfonamido)benzamideYield 106.3%

Procedure

(S)-2-(1-((5-Bromo-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 (170 mg, 0.29 mmol) was treated with N, N-dimethyl-3-(methylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (262 mg, 0.71 mmol), sodium carbonate (75 mg, 0.71 mmols) and bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (74 mg, 0.09 mmol) according to the method described in Preparation 62. The residue was purified using SP1® Purification System (0% to 100%, dichloromethane-ethyl acetate) to give 233 mg (99% yield) of the title compound. Purity 92%.

Workup

  1. customdescribed in Preparation 62
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 100%, dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-c758291f33bf4507ae52e6391d575a83
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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