Hydrochloric Acid → 3-(4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydrofuran-3-yl)phenyl)-3-fluoroazetidine hydrochloride

HRID 2277735Notes

Reaction equation

HRID 2277735 reaction equation
C(OC([N:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:23][C:22]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)([C:24]([F:27])([F:26])[F:25])[O:21][CH:20]=3)=[CH:15][CH:14]=2)([F:12])[CH2:9]1)=O)(C)(C)C.Cl>CO>[ClH:34].[Cl:35][C:30]1[CH:29]=[C:28]([C:22]2([C:24]([F:26])([F:25])[F:27])[O:21][CH:20]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:10]4([F:12])[CH2:9][NH:8][CH2:11]4)=[CH:14][CH:15]=3)[CH2:23]2)[CH:33]=[C:32]([Cl:34])[CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 897256703-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-phenyl}-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 897253993-(4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydrofuran-3-yl)phenyl)-3-fluoroazetidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-phenyl}-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester (Example 1, Intermediate 2) (0.45 g, 0.845 mmol) in MeOH (10 mL) was purged HCl gas for 1 hour at room temperature. After consumption of starting material, reaction mixture concentrated in vacuo to get pale yellow semisolid (0.49 g, crude), which was triturated with n-pentane (2×5 mL) to get off product as white solid. Yield: 0.36 g, 98.53%. 1H NMR (400 MHz, DMSO-d6) δ: 3.20 (d, J=17.16 Hz, 1H), 3.64 (d, J=17.16 Hz, 1H), 4.30-4.54 (m, 4H), 7.29 (d, J=7.96 Hz, 2H), 7.48 (s, 1H), 7.52 (d, J=8 Hz, 2H), 7.69-7.71 (m, 3H), 9.36 (bs, 2H).

Workup

  1. customAfter consumption of starting material, reaction mixture
  2. concentrationconcentrated in vacuo
  3. customto get pale yellow semisolid (0.49 g, crude), which
  4. customwas triturated with n-pentane (2×5 mL)
  5. customto get off product as white solid

Sources & evidence

ORD record
ord-b4353b34338a4470a3f87384adb5e99d
Source dataset
uspto-grants-2015_09
Patent number
US09133172B2

Reaction notes

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