Hydrochloric Acid → HCID 178483356, compound

HRID 1007550Notes

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.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH2:27][CH2:28][CH:29]=O.Cl>>[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH2:27][CH2:28][CH2:29][N:2]([CH3:1])[C@H:3]1[CH2:4][CH2:5][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)[CH2:7][CH2:8]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 218597273-(2,4-Dichlorophenyl)propanal

HCID 178484782HCID 178484782, compound

Product 1

HCID 178483356HCID 178483356, compoundYield 54.2%

Procedure

Condensation of 15 (550 mg, 1.9 mmol) and 3-(2,4-dichlorophenyl)-propionaldehyde (390 mg, 1.9 mmol) following the procedure described in Example 45, Step 2, followed by conversion to the HCl salt, gave 6-(trans-4-{[3-(2,4-dichlorophenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (446 mg, 50%), as an off-white solid: mp 273-279° C.; IR (KBr): 2949, 1775, 1500, 1474 cm−1; 1H NMR(500 MHz, DMSO-d6): δ 11.49 (s, 1H), 10.01 (s, 1H), 7.61 (d, J=2 Hz, 1H), 7.47-7.41 (m, 2H), 7.17 (s, 1H), 7.00 (s, 2H), 3.34-3.29 (m, 1H), 3.22-3.17 (m, 1H), 3.11-3.03 (m, 1H), 2.79-2.73 (m, 2H), 2.71 (d, J=5 Hz, 3H), 2.59-2.48 (m, 1H), 2.14-2.06 (m, 2H), 2.03-1.97 (m, 2H), 1.94-1.88 (m, 2H), 1.69-1.50 (m, 4H); ESI (m/z): 433 [M+H]+; HPLC: method A, 6.78 minutes (>99%); Anal. Calcd for C23H26Cl2N2O2.HCl: C, 58.80; H, 5.79; N, 5.96. Found: C, 58.62; H, 5.76; N, 5.89.

Sources & evidence

ORD record: ord-71c009d6dd7847c6a2cdc80eff4bab4a
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794402B2

Reaction notes

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