Benzoic Acid → Benzoate

HRID 1893731Notes

Reaction equation

HRID 1893731 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:37]=[CH:36][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[N:29]=[C:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:27]=[CH:26][N:25]=4)[CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:38]([OH:46])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[N:29]=[C:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:27]=[CH:26][N:25]=4)[CH:17]=3)=[O:14])=[CH:36][CH:37]=2)[CH2:4][CH2:3]1.[C:38]([O-:46])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 5291Imatinib

Product 2

HCID 242BenzoateHCID 5291Imatinib

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide (4.94 g, 10 mmol) is added to a solution of benzoic acid (Fluka, Buchs, Switzerland; 1.22 g, 10 mmol) in xylene (50 mL). The mixture is heated and the resulting hot solution is filtered. Upon cooling, the product crystallizes and is filtered and dried to afford 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide, benzoate as a pale-brown crystalline solid, having the following analytical properties: Analysis found: C, 70.13; H, 6.12; N, 16.24%. Calculated for C36H37O3: C, 70.22; H, 6.06; N, 15.92%.

Workup

  1. temperatureThe mixture is heated
  2. filtrationthe resulting hot solution is filtered
  3. temperatureUpon cooling
  4. customthe product crystallizes
  5. filtrationis filtered
  6. customdried

Sources & evidence

ORD record
ord-3f9826809fd244e38f3e62869cbba04d
Source dataset
uspto-grants-2013_08
Patent number
US08513256B2

Reaction notes

Loading…