Acetaldehyde → HCID 178464514, compound

HRID 1007526Notes

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 178461708HCID 178461708, compound

Product 1

HCID 178464514HCID 178464514, compoundYield 52.1%

Procedure

Coupling of 6-{trans-4-[(S)-1-methyl-3-phenylpropylamino]cyclohexyl}-3H-benzoxazol-2-one (196 mg, 0.538 mmol) and acetaldehyde (24 mg, 0.538 mmol) following the procedure described in Example 24, followed by formation of the HCl salt, gave 6-(trans-4-{ethyl-[(S)-1-methyl-3-phenylpropyl]-amino}cyclohexyl)-3H-benzoxazol-2-one (110 mg, 50%), as a pale yellow solid (a mixture of diastereomers): mp 221-246° C.; IR (KBr): 3424, 2929, 1771, 1495 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), 126 (m, 6H); API-MS (methane) (m/z): 393 [M+H]+; HPLC: method C, 5.88 minutes (97.4%), method D, 11.32 minutes (>99%); Anal. Calcd for C25H32N2O2.HCl.H2O: C, 67.17; H, 7.89; N, 6.27. Found: C, 67.18; H, 7.69; N, 5.98.

Sources & evidence

ORD record: ord-736914daca4a4720b25db8347b31b2d3
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794402B2

Reaction notes

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