Hydrochloric Acid → HCID 44128661, compound

HRID 1514256Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[CH2:26][N:25]([CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[CH2:24][CH2:23][CH2:22][C:21]=4[CH:35]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl>CCOCC.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[CH2:26][N:25]([CH2:27][C:28]([OH:30])=[O:29])[CH2:24][CH2:23][CH2:22][C:21]=4[CH:35]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

1,1-Dimethylethyl [7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]acetate (Preparation 8) (65 mg, 0.131 mmol) was treated with HCl (1305 μl, 5.22 mmol) (4N in dioxan) and left standing for 2 hours. The reaction mixture was then warmed at 50° C. for 1 hour then heated at 60° C. for a further 1.25 hours before solvent removal by evaporation. Trituration with ether/EtOAc failed and the material obtained was purified by MDAP. A white solid (20 mg) was obtained freeze drying appropriate MDAP fractions. Further drying under vacuum at 70° C. for 16 hours yielded the title compound (16 mg) as a solid. δH (400 MHz, d6DMSO) 1.36 (6H, d), 1.51-1.53 (2H, m), 2.98-3.00 (2H, m), 3.4 (2H, br.s), 4.10 (2H, s), 4.86-4.92 (1H, m), 7.32 (1H, d), 7.44 (1H, d), 7.83-7.88 (2H, m), 8.11 (1H, dd), 8.18 (1H, d); MS (ES) C23H2435ClN3O4 requires 441; found 442 [M+H]+.

Workup

waitleft
temperaturethen heated at 60° C. for a further 1.25 hours before solvent removal by evaporation
customthe material obtained
customwas purified by MDAP

Sources & evidence

ORD record: ord-a2e784f7627646a3a294e4ac23ed2f07
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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