Hydrochloric Acid → HCID 178483373, compound

HRID 1007552Notes

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.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[C:21]=1[CH2:28][CH2:29][CH:30]=O.Cl>>[F:27][C:22]1[CH:23]=[C:24]([F:26])[CH:25]=[C:20]([F:19])[C:21]=1[CH2:28][CH2:29][CH2:30][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 226691263-(2,4,6-Trifluorophenyl)propanal

HCID 178484782HCID 178484782, compound

Product 1

HCID 178483373HCID 178483373, compoundYield 34.6%

Procedure

Condensation of 15 (460 mg, 1.9 mmol) and 3-(2,4,6-trifluorophenyl)-propionaldehyde (360 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-(2,4,6-trifluorophenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (275 mg, 32%), as a white solid: mp 235-238° C.; IR (KBr): 2949, 1772, 1632, 1603 cm−1; 1H NMR (300 MHz, DMSO-d6): δ 11.54 (s, 1H), 9.78 (s, 1H), 7.26-7.18 (m, 3H), 7.00 (s, 2H), 3.32-3.27 (m, 1H), 3.26-3.04 (m, 2H), 2.71 (d, J=5 Hz, 3H), 2.58-2.54 (m, 1H), 2.66-2.62 (m, 2H), 2.12-1.86 (m, 6H), 1.68-1.48 (m, 4H); ESI (m/z): 419 [M+H]+; HPLC: method A, 6.30 minutes (98.8%); Anal. Calcd for C23H25F3N2O2.HCl: C, 60.73; H, 5.76; N, 6.16. Found: C, 60.43; H, 5.71; N, 5.99.

Sources & evidence

ORD record: ord-224c994e3308478399b47e24a021df4e
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794402B2

Reaction notes

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