Acetaldehyde → HCID 178464515, compound

HRID 1007525Notes

Reaction equation

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

Participants

Reactant 3

HCID 177Acetaldehyde

HCID 313Hydrochloric Acid

HCID 178461709HCID 178461709, compound

Product 1

HCID 178464515HCID 178464515, compoundYield 25%

Procedure

Coupling of 6-{trans-4-[(R)-1-methyl-3-phenylpropylamino]cyclohexyl}-3H-benzoxazol-2-one (370 mg, 1.01 mmol) and acetaldehyde (44 mg, 1.01 mmol) following the procedure described in Example 24, followed by formation of the HCl salt, gave 6-(trans-4-{ethyl-[(R)-1-methyl-3-phenylpropyl]amino}-cyclohexyl)-3H-benzoxazol-2-one (70 mg, 25%), as a pale yellow solid (a mixture of diastereomers): mp 139-158° C.; IR (KBr): 2941, 1772, 1497, 1451 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.52 (s, 2H), 9.11 (s, 2H), 7.35-7.21 (m, 10H), 7.18 (m, 4H), 7.00 (s, 2H), 3.20 (m, 2H), 2.81 (m, 2H), 2.54 (m, 2H), 2.20-1.51 (m, 28H), 1.44 (d, J=7 Hz, 3H), 1.32 (d, J=7 Hz, 3H), 1.26 (m, 6H); API-MS (methane) (m/z): 393 [M+H]+; calcd for C25H32N2O2, 393.2542; found, 393.2540; HPLC: method C, 5.77 minutes (97.4%), method D, 11.47 minutes and 11.57 minutes (98.1%); Anal. Calcd for C25H32N2O2HCl.0.5H2O: C, 68.55; H, 7.82; N, 6.40. Found: C, 68.67; H, 8.03; N, 6.27.

Sources & evidence

ORD record: ord-29bee5072f9b42be85ce71641f622ddf
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794402B2

Reaction notes

Loading…