Triethylamine → N-[4-Chloro-3-(4-methylpiperazin-1-yl)phenyl]-N'-[4-(pyridin-4-yl)naphth-1-yl]urea

HRID 1275017

Reaction equation

HRID 1275017 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[N:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([NH2:29])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C.[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][C:39]=1[N:45]1[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]1>ClCCl>[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][C:2]([NH:29][C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]([C:16]3[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=3)=[CH:20][CH:21]=2)=[O:4])=[CH:40][C:39]=1[N:45]1[CH2:46][CH2:47][N:48]([CH3:51])[CH2:49][CH2:50]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 108570124-(Pyridin-4-yl)naphth-1-ylamineHCID 181800734-Chloro-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 22118919N-[4-Chloro-3-(4-methylpiperazin-1-yl)phenyl]-N'-[4-(pyridin-4-yl)naphth-1-yl]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of triphosgene (39 mg, 0.13 mmole) in dichloromethane (10 ml) was added a solution of 4-(pyridin-4-yl)naphth-1-ylamine (D1, 82 mg, 0.37 mmole) and triethylamine (0.05 ml, 0.37 mmole) dropwise over 30 minutes. When the addition was complete the mixture was stirred at room temperature for 15 minutes, then a solution of 4-chloro-3-(4-methylpiperazin-1-yl)aniline (100 mg, 0.44 mmole, EP0533268A1) in dichloromethane (10 ml) was added over 5 minutes. After 18 h, the mixture was washed with 10% aqueous sodium carbonate solution and water, dried (Na2SO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 10% methanol/dichloromethane and the title compound was obtained as a white solid on trituration with ether (47 mg, 27%).

Workup

  1. additionWhen the addition
  2. waitAfter 18 h
  3. washthe mixture was washed with 10% aqueous sodium carbonate solution and water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel eluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-58d818f6374b4e928a506fea67f2417a
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Linked notes

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