Hydrochloric Acid → N-(2-aminophenyl)-4-{3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzamide

HRID 599511Notes

Reaction equation

HRID 599511 reaction equation
[C:1]([C:3]1[C:4]([C:19]2[CH:41]=[CH:40][C:22]([C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[NH:32]C(=O)OC(C)(C)C)=[O:24])=[CH:21][CH:20]=2)=[N:5][CH:6]=[C:7]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)[CH:8]=1)#[N:2].Cl.O>C(OCC)(=O)C>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][C:7]([CH2:9][N:10]3[CH2:15][CH2:14][N:13]([CH:16]([CH3:17])[CH3:18])[CH2:12][CH2:11]3)=[CH:6][N:5]=2)=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 962WaterHCID 86624986HCID 86624986, compound

Product 1

HCID 11539751N-(2-aminophenyl)-4-{3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

t-Butyl {2-[(4-{3-cyano-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzoyl)amino]phenyl}carbamate (586 mg, 1.06 mmol; prepared as described in Method 19) was dissolved in ethyl acetate (7 ml) and 3M aqueous hydrochloric acid (7 ml) was added. The resulting suspension was stirred for 6 hours at ambient temperature then 3M aqueous hydrochloric acid (1.75 ml) added. The suspension was stirred for a further 2 hours then 3M aqueous hydrochloric acid (3.5 ml) was added and stirred for 30 minutes. The suspension was poured into water (50 ml) and washed with ethyl acetate (3×15 ml). The resulting aqueous solution was basified using a 2M aqueous solution of sodium hydroxide. A pale yellow precipitate crashed out which was filtered and washed with water. The pale yellow solid was dried in a vacuum oven at 50° C. ovenight (294 mg, 62%); NMR Spectrum: (CDCl3) 0.99 (d, 6H), 2.48 (m, 8H), 2.60 (m, 1H) 3.56 (s, 2H), 3.79 (br s, 2H), 6.80 (m, 2H), 7.03 (m, 1H), 7.32 (d, 1H), 7.81 (br s, 1H), 7.99 (s, 4H), 8.04 (s, 1H), 8.74 (s, 1H); Mass Spectrum: M+H+ 455.

Workup

  1. stirringThe suspension was stirred for a further 2 hours
  2. stirringstirred for 30 minutes
  3. washwashed with ethyl acetate (3×15 ml)
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe pale yellow solid was dried in a vacuum oven at 50° C. ovenight (294 mg, 62%)

Sources & evidence

ORD record
ord-f1c5e2a2811e44d4a70168cb6b90bac6
Source dataset
uspto-grants-2011_03
Patent number
US07897778B2

Reaction notes

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