Hydrochloric Acid → HCID 11373433, compound

HRID 2354171Notes

Reaction equation

HRID 2354171 reaction equation
[CH2:1](OC(OCC)OCC)C.[NH2:11][C:12]1[CH:33]=[C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)[CH:31]=[CH:30][C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[C:21]([C:23]([NH:25][CH:26]2[CH2:28][CH2:27]2)=[O:24])[CH:20]=[CH:19][C:18]=1[CH3:29])=[O:15].Cl.C(=O)(O)[O-].[Na+]>C(O)C.C(O)(=O)C>[CH:26]1([NH:25][C:23](=[O:24])[C:21]2[CH:20]=[CH:19][C:18]([CH3:29])=[C:17]([N:16]3[C:14](=[O:15])[C:13]4[C:12](=[CH:33][C:32]([N:34]5[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]5)=[CH:31][CH:30]=4)[N:11]=[CH:1]3)[CH:22]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 66918880HCID 66918880, compound

Product 1

HCID 11373433HCID 11373433, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Triethylorthoformate (0.18 ml) was added to a stirred mixture of 2-amino-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-(4-methylpiperazin-1-yl)benzamide (0.152 g) and glacial acetic acid (0.011 ml) in ethanol (30 ml). The mixture was heated to 90° C. and stirred for 16 hours. To the mixture was added 1N HCl (1 ml) and heated to 90° C. for 2 hours. The reaction mixture was made basic with sodium bicarbonate and evaporated, dissolved in ethyl acetate and washed with water. The organic phase was dried (magnesium sulphate) and evaporated to give the title compound (0.098 g); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.70 (m, 2H), 2.13 (s, 3H), 2.31 (s, 3H), 2.56 (m, 4H), 2.86 (m, 1H), 3.44 (m, 4H), 7.05 (d, 1H), 7.27 (m, 1H), 7.51 (d, 1H), 7.80 (d, 1H), 7.89 (m, 1H), 7.99 (d, 1H), 8.16 (s, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 418.

Workup

  1. temperatureheated to 90° C. for 2 hours
  2. customevaporated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-03ecd8954e0240fcbdfba2a426e96835
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

Loading…