Water → HCID 71542728, compound

HRID 1402530Notes

Reaction equation

HRID 1402530 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:31]=4[F:37])=[O:28])=[CH:22][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[NH:10][CH:9]=1)=[O:7].C(N(CC)C(C)C)(C)C.Br[CH2:48][C:49]([O:51][CH3:52])=[O:50].O>CN(C=O)C>[F:37][C:31]1[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:30]=1[NH:29][C:27]([NH:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:11]3[NH:10][CH:9]=[C:8]([C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:48][C:49]([O:51][CH3:52])=[O:50])=[O:7])[CH:12]=3)[CH:18]=2)=[CH:25][CH:24]=1)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 71293513HCID 71293513, compound

Product 1

HCID 71542728HCID 71542728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(3-aminopropyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamide (260 mg, 0.52 mmol) and N,N-diisopropylethylamine (134 mg, 1.04 mmol) in 10 ml of anhydrous DMF was added methyl bromoacetate (80 mg, 0.52 mmol). The mixture was stirred at room temperature for 40 minutes and poured into 100 ml of water with vigorous stirring. The precipitates were filtered and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with a gradient of 3˜10% MeOH/CHCl3 to afford methyl [(3-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}propyl)amino]acetate as white solid. Yield: 100 mg, 34%.

Workup

  1. filtrationThe precipitates were filtered
  2. customdried in vacuo
  3. customto give the crude, which
  4. customwas purified by silica gel chromatography
  5. washeluting with a gradient of 3˜10% MeOH/CHCl3

Sources & evidence

ORD record
ord-718e901b341d419ea62f5592d5ad4f36
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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