Hydrazine → HCID 59419560, compound

HRID 2387184Notes

Reaction equation

HRID 2387184 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[CH:5]=1.[NH2:25][NH2:26]>CCO>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=3[CH3:10])[C:3]([NH:25][NH2:26])=[O:2])[N:17]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 17748019Methyl 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoate

Product 1

HCID 59419560HCID 59419560, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid methyl ester 4 (3.2 g, 10 mmol) and hydrazine (6 mmol) are dissolved in dry EtOH (20 mL) and heated at reflux overnight. The mixture is cooled to room temperature. The solid is filtered, washed with water and dried under vacuum overnight to afford the product 6 as a light yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 9.68 (s, 1H), 9.26 (m, 1H), 9.06 (s, 1H), 8.69 (dd, J=4.7, 1.5H, 1H), 8.52 (d, J=5.1, 1.2 Hz, 1H), 8.43 (m, 1H), 8.1 (dd, J=5.8, 1.6 Hz, 1H), 7.56 (m, 2H), 7.46 (dd, J=5.1, 1.6 Hz, 1H), 7.3 (d, J=7.9 Hz, 1H), 4.45 (s, 1H), 3.33 (s, 3H), 3.31 (s, 1H). MS (m/z) (M+1)+: 321.1.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationThe solid is filtered
  4. washwashed with water
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-550abacf7a644d999b1cef11abef9ccf
Source dataset
uspto-grants-2012_09
Patent number
US08268850B2

Reaction notes

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