Sodium Carbonate → (S)-N-(3-Hydroxy-5-(4-((3-hydroxy-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamide

HRID 1052622Notes

Reaction equation

HRID 1052622 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:16]3[N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:20](=[O:28])[C:19]4=[C:29]([CH3:32])[CH:30]=[CH:31][N:18]4[N:17]=3)[CH2:13][CH2:14][OH:15])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:3]=1.[OH:41][C:42]1[CH:43]=[C:44]([NH:57][S:58]([CH3:61])(=[O:60])=[O:59])[CH:45]=[C:46](B2OC(C)(C)C(C)(C)O2)[CH:47]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[OH:41][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:16]4[N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:20](=[O:28])[C:19]5=[C:29]([CH3:32])[CH:30]=[CH:31][N:18]5[N:17]=4)[CH2:13][CH2:14][OH:15])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:3]=2)[CH:47]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 72219545N-(3-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)methanesulfonamideHCID 131736236(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-3-hydroxypropyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 131736237(S)-N-(3-Hydroxy-5-(4-((3-hydroxy-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)methanesulfonamideYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-3-hydroxypropyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.08 mmol) was treated with N-(3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (85 mg, 0.21 mmol), sodium carbonate (23 mg, 0.22 mmols) and 1,11-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (21 mg, 0.03 mmol) in 1,2-dimethoxyethane (1.6 ml) and water (0.40 ml) according to the method described in Preparation 62. The residue was purified using SP1® Purification System (0% to 100%, hexane-ethyl acetate) to give 35 mg (39% yield, 65% purity) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-08667cb0f3d04cda8dc8b1a79feaf476
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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