Sodium Hydroxide → HCID 22669086, compound

HRID 1007538Notes

Reaction equation

HRID 1007538 reaction equation
C[N:2]([CH:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:29]=[CH:28][C:23]3[NH:24][C:25](=[O:27])[O:26][C:22]=3[CH:21]=2)[CH2:16][CH2:15]1)[CH2:3][CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>C(Cl)Cl>[O:27]=[C:25]1[NH:24][C:23]2[CH:28]=[CH:29][C:20]([CH:17]3[CH2:16][CH2:15][CH:14]([NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:13])[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:19][CH2:18]3)=[CH:21][C:22]=2[O:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22669087HCID 22669087, compound

Product 1

HCID 22669086HCID 22669086, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Coupling of N-(2-{methyl-[4-(2-oxo-2,3-dihydrobenzoxazol-6-yl)cyclohexyl]amino}ethyl)benzamide (755 mg, 1.81 mmol) and p-formaldehyde (0.50 mL of a 37 wt % aqueous solution, 6.1 mmol), following the procedure described in Example 17 except NaOH (1.8 mL of a 1.0N aqueous solution, 1.8 mmol) and CH2Cl2 (5 mL) were added, gave N-{2-[4-(2-oxo-2,3-dihydrobenzoxazol-6-yl)cyclohexylamino]ethyl}benzamide (528 mg, 66%), as a white solid (a mixture of cis/trans isomers): mp 167-175° C.; IR (KBr): 2940, 1770, 1647 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.51 (s, 1H), 10.41 (br s, 0.7H), 10.03 (br s, 0.3H) 8.96-8.94 (m, 1H), 8.00-7.92 (m, 2H), 7.60-7.40 (m, 3H), 7.15 (s, 1H), 7.00 (s, 1H), 3.79-3.65 (m, 2H), 3.45-3.19 (m, 2H), 2.82-2.79 (m, 4H), 2.58-2.50 (m, 1H), 2.20-2.10 (m, 2H), 1.92-1.81 (m, 3H), 1.70-1.51 (m, 4H); ESI-MS (m/z): 394 [M+H]+; HPLC: method A, 4.89 minutes (95.0%); method B, 10.0 minutes (>99%); Anal. Calcd for C23H27FN3O3.HCl.0.75H2O: C, 62.30; H, 6.71; N, 9.48. Found: C, 62.43; H, 6.68; N, 9.62.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-6cf0c2644685465993c15ec997d23e88
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

Loading…