Water → HCID 71293579, compound

HRID 1402578Notes

Reaction equation

HRID 1402578 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].[OH2:53].C1[CH2:58][O:57][CH2:56][CH2:55]1>>[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][N:1]([CH2:55][C:56]([O:57][CH3:58])=[O:53])[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 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 71293513HCID 71293513, compound

Product 1

HCID 71293579HCID 71293579, compound

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of N-(3-aminopropyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamide (200 mg, 0.40 mmol) and N,N-diisopropylethylamine (0.5 ml, 2.8 mmol) in 10 ml of anhydrous THF was added methyl bromoacetate (200 mg, 1.30 mmol). The mixture was heated at 60° C. for 16 hours 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 5% of MeOH in CHCl3 to afford dimethyl 2,2′-[(3-{[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}propyl)imino]diacetate as white solid. Yield: 210 mg, 82%.

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 5% of MeOH in CHCl3

Sources & evidence

ORD record
ord-27563734e91f4b2e9b85e0ee5cc87d54
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

Loading…