Methylamine → HCID 53946703, compound

HRID 1005593Notes

Reaction equation

HRID 1005593 reaction equation
[CH3:1][C@H:2]([O:16][C:17]1[CH:59]=[CH:58][CH:57]=[CH:56][C:18]=1[C:19]([NH:21][C:22]1[CH:53]=[CH:52][C:25]([C:26]([N:28]([CH3:51])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=2[O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([N:44]2[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]2)=[O:43])=[O:27])=[CH:24][C:23]=1[O:54][CH3:55])=[O:20])[CH2:3][CH2:4][N:5]1C(=O)C2=CC=CC=C2C1=O.CN>CO>[NH2:5][CH2:4][CH2:3][C@@H:2]([O:16][C:17]1[CH:59]=[CH:58][CH:57]=[CH:56][C:18]=1[C:19]([NH:21][C:22]1[CH:53]=[CH:52][C:25]([C:26]([N:28]([CH3:51])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=2[O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([N:44]2[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]2)=[O:43])=[O:27])=[CH:24][C:23]=1[O:54][CH3:55])=[O:20])[CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 54455786HCID 54455786, compound

Product 1

HCID 53946703HCID 53946703, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (S)-4-[2-[1-methyl-3-(phthalimido)prop-1-yl]oxybenzoyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (1.1 g) in methanol (30 ml) was stirred and treated with 40% methylamine in methanol (10 ml). The reaction mixture was refluxed for 30 minutes. Then the solvent was concentrated and purified by silica gel column chromatography (SiO2 40 g, chloroform/methanol/ammonia=90/10/0.5) to give (S)-4-[2-[(3-amino-1-methylprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. concentrationThen the solvent was concentrated
  3. custompurified by silica gel column chromatography (SiO2 40 g, chloroform/methanol/ammonia=90/10/0.5)

Sources & evidence

ORD record
ord-f215c9f925154852b5bde9d18d540442
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

Loading…