Hydrazine hydrate (1:1) → 3-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid hydrazide

HRID 387218Notes

Reaction equation

HRID 387218 reaction equation
CO[C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:33](=[O:34])[N:32]([CH2:35][CH3:36])[C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:16]=[CH:17][C:12]=3[CH:11]=2)=[C:6]([Cl:37])[CH:5]=1.[OH2:39].[NH2:40][NH2:41]>C(O)C>[Cl:37][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[C:10]1[C:33](=[O:34])[N:32]([CH2:35][CH3:36])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[CH:23][CH:24]=3)[N:16]=[CH:17][C:12]=2[CH:11]=1)[C:3]([NH:40][NH2:41])=[O:39]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 671196003-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid methyl ester

Product 1

HCID 671196213-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid hydrazideYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-4-{8-ethyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}benzoic acid methyl ester (6, 77 mg, 0.14 mmol) in the mixture of ethanol (4 mL) and hydrazine hydrate (1 mL) was heated at reflux for 2 h. The reaction mixture was cooled and the yellow precipitate was collected and washed with 2-propanol and diethyl ether to afford the title compound (40 mg, 0.08 mmol, 57%) as a yellow solid. ESMS m/z 533 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.94 (br. s., 2H) 8.77 (s, 1H) 7.95 (d, J=1.5 Hz, 1H) 7.87 (s, 1H) 7.83 (dd, J=7.8, 1.5 Hz, 1H) 7.66 (d, J=9.0 Hz, 2H) 7.51 (d, J=7.8 Hz, 1H) 6.94 (d, J=9.0 Hz, 2H) 4.56 (br. s., 2H) 4.36 (q, J=7.0 Hz, 2H) 3.05-3.15 (m, 4H) 2.42-2.48 (m, 4H) 2.22 (s, 3H) 1.28 (t, J=7.0 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction mixture was cooled
  4. customthe yellow precipitate was collected
  5. washwashed with 2-propanol and diethyl ether

Sources & evidence

ORD record
ord-6b0ace76e17c4143be39f5a1183c3565
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

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