Methanol → HCID 57550278, compound

HRID 1642217Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:33])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+].CO>C(Cl)Cl>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:25]=[CH:24][C:23]([O:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:33])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(4-Trifluoromethyl-phenoxy)-phenylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (HVB01063, 1.0 g, 2.16 mmol) was dissolved in DCM (20 ml), and cooled to 0° C., and to this was added TFA (5 ml). Allowed to warm to room temperature and stirred for 1 h. The solution was poured over solid potassium carbonate (12 g), and extracted with DCM and water. Organic layers dried over MgSO4 and evaporated to dryness, to afford a cream coloured solid. 0.85 g, 100%, R.f. 0.4 (5% MeOH in DCM), 1HNMR: (CDCl3, 270 MHz) δ 1.65 (2H, m, CHCH2), 1.79 (2H, m, CHCH2), 2.30 (1H, m, CH), 2.64 (2H, td, J=12.4, 2.7 Hz, NCH2), 3.10 (2H, m, NCH2), 6.97 (1H, dd, J=6.4, 30.5 Hz, Ar HD), 7.05 (2H, m, Ar HF), 7.06 (1H, m, Ar HB), 7.17 (1H, t, J=7.2 Hz, Ar HC), 7.58, D, J=8.6 Hz, Ar HE), 8.39 (1H, d, J=7.9 Hz, Ar HA).

Workup

temperatureAllowed to warm to room temperature
extractionextracted with DCM and water
dry with materialOrganic layers dried over MgSO4
customevaporated to dryness
customto afford a cream

Sources & evidence

ORD record: ord-8873911782604bf2af7275abf02ee285
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119627B2

Reaction notes

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