Hydrochloric Acid → HCID 178483363, compound

HRID 1007537Notes

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 6344Dichloromethane

HCID 178518617HCID 178518617, compound

Product 1

HCID 178483363HCID 178483363, compoundYield 52%

Procedure

Condensation of 6-(trans-4-[3-(3,4-difluorophenyl)propylamino]-cyclohexyl}-3H-benzoxazol-2-one (400 mg, 1.0 mmol) with p-formaldehyde (740 mg, 24.7 mmol) following the procedure described in Example 17, except CH2Cl2 (15 mL) was also added, followed by formation of the HCl salt, gave 6-(trans-4-{[3-(3,4-difluorophenyl)propyl]methylamino}cyclohexyl)-3H-benzoxazol-2-one (226 mg, 52%), as a white solid: mp 224-227° C.; IR (KBr): 2945, 1764 cm−1; 1H NMR (500 MHz, DMSO-d6):, δ 11.50 (s, 1H), 9.94 (s, 1H), 7.40-7.34 (m, 2H), 7.16 (s, 1H), 7.12-7.09 (m, 1H), 7.00 (s, 2H), 3.33-3.29 (m, 1H), 3.18-3.11 (m, 1H), 3.03-2.97 (m, 1H), 2.71 (d, J=5 Hz, 3H), 2.68-2.63 (m, 2H), 2.59-2.50 (m, 1H), 2.14-1.98 (m, 4H), 1.94-1.88 (m, 2H), 1.66-1.51 (m, 4H); ESI-MS (m/z): 401 [M+H]+; HPLC: method A, 5.97 minutes (97.1%); Anal. Calcd for C23H26F2N2O2.HCl: C, 63.23; H, 6.23; N, 6.41. Found: C, 62.94; H, 6.56; N, 6.32.

Workup

additionwas also added

Sources & evidence

ORD record: ord-4a63bab201ea4079b5a6461df94b3d39
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794402B2

Reaction notes

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