Hydrochloric Acid → HCID 178440851, compound

HRID 1007551Notes

Reaction equation

[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:18]=[CH:17][C:12]3[NH:13][C:14](=[O:16])[O:15][C:11]=3[CH:10]=2)[CH2:5][CH2:4]1.[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]=O)=[CH:25][CH:24]=1)[CH:20]([CH3:22])[CH3:21].Cl>>[CH2:19]([C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][CH2:31][N:2]([CH3:1])[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]3[CH:18]=[CH:17][C:12]4[NH:13][C:14](=[O:16])[O:15][C:11]=4[CH:10]=3)[CH2:7][CH2:8]2)=[CH:27][CH:28]=1)[CH:20]([CH3:21])[CH3:22]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 156066493-(4-(2-Methylpropyl)phenyl)propanal

HCID 178484782HCID 178484782, compound

Product 1

HCID 178440851HCID 178440851, compoundYield 64.5%

Procedure

Condensation of 15 (1.0 g, 3.6 mmol) and 3-(4-isobutylphenyl)-propionaldehyde (700 mg, 3.6 mmol), following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(4-isobutylphenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (977 mg, 61%), as an off-white solid: mp 162-165° C.; IR (KBr): 2953, 1773, 1498, 1451 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 11.55 (s, 1H), 10.00 (s, 1H), 7.17-7.08 (m, 5H), 7.00 (s, 2H), 3.32-3.28 (m, 1H), 3.21-3.08 (m, 1H), 3.08-2.95 (m, 1H), 2.70 (d, J=5 Hz, 3H), 2.65-2.52 (m, 3H), 2.41 (d, J=7 Hz, 2H), 2.14-1.73 (m, 7H), 1.68-1.49 (m, 4H), 0.85 (d, J=7 Hz, 6H); HRMS-API (m/z): [M+H]+ calcd for C27H36N2O2, 421.2855; found, 421.2858; HPLC: method A, 7.49 minutes (>99%); method B, 13.59 minutes (>99%); Anal. Calcd for C27H36N2O2.HCl.0.5H2O: C, 69.58; H, 8.22; N, 6.01. Found: C, 69.23; H, 8.20; N, 5.87.

Sources & evidence

ORD record: ord-654b96574302437aa1ee6a3bf9691476
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794402B2

Reaction notes

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