Water → HCID 71542729, compound

HRID 1402531Notes

Reaction equation

HRID 1402531 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=4[F:36])=[O:27])=[CH:21][CH:20]=3)[CH:15]=[CH:14][N:13]=2)[NH:9][CH:8]=1)=[O:6].C(N(CC)C(C)C)(C)C.Br[CH2:47][C:48]([O:50][CH3:51])=[O:49].O>CN(C=O)C>[F:36][C:30]1[CH:31]=[CH:32][C:33]([CH3:35])=[CH:34][C:29]=1[NH:28][C:26]([NH:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:16]2[CH:15]=[CH:14][N:13]=[C:12]([C:10]3[NH:9][CH:8]=[C:7]([C:5]([NH:4][CH2:3][CH2:2][NH:1][CH2:47][C:48]([O:50][CH3:51])=[O:49])=[O:6])[CH:11]=3)[CH:17]=2)=[CH:20][CH:21]=1)=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 71293548HCID 71293548, compound

Product 1

HCID 71542729HCID 71542729, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(2-aminoethyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamide (200 mg, 0.41 mmol) in 10 ml of anhydrous DMF, were added N,N-diisopropylethylamine (137 mg, 1.06 mmol) and methyl bromoacetate (82 mg, 0.54 mmol). The mixture was stirred at room temperature for 1 hour and poured into 100 ml of water. The precipitates were filtered, washed with water, and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with a gradient of 3˜8% of methanol in chloroform to give methyl [(2-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}ethyl)amino]acetate as white solid. Yield: 100 mg, 43%.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo
  4. customto give the crude, which
  5. customwas purified by silica gel chromatography
  6. washeluting with a gradient of 3˜8% of methanol in chloroform

Sources & evidence

ORD record
ord-1050b2d92ba24734bcb752d2f16eee25
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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