Hydrochloric Acid → HCID 59455267, compound

HRID 1401716Notes

Reaction equation

[CH3:1][N:2]1[CH2:30][CH2:29][C:5]2[N:6]([CH2:14][C:15]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:16][C:17]([O:19]CC)=[O:18])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[OH-].[K+].Cl>CN1C(=O)CCC1>[CH3:1][N:2]1[CH2:30][CH2:29][C:5]2[N:6]([CH2:14]/[C:15](/[C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)=[CH:16]/[C:17]([OH:19])=[O:18])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 4-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-3-(4-fluorophenyl)but-2-enoate (100 mg, 0.246 mmol) was dissolved in NMP (1 mL). Powdered KOH (100 mg) was added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to RT and acidified with conc. HCl (pH 5-6). The product was isolated by reverse phase chromatography. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.40 (d, 1H), 7.18 (m, 3H), 7.05 (m, 1H), 6.90 (m, 2H), 6.10 (s, 1H), 5.90 (m, 1H), 5.70 (m, 1H), 4.50 (m, 2H), 4.22 (m, 2H), 3.70 (m, 2H), 3.0 (s, 3H), 2.40 (s, 3H).

Workup

temperatureThe reaction mixture was cooled to RT
customThe product was isolated by reverse phase chromatography

Sources & evidence

ORD record: ord-45010da5b9a8415c923cac769195f22b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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