Hydrochloric Acid → HCID 86684790, compound

HRID 472708Notes

Reaction equation

HRID 472708 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH2:13][N:14]([CH3:38])[C:15]([N:17]2[CH2:29][CH2:28][C@:20]3([NH:24][C@@H:23]([C:25]([NH2:27])=[O:26])[CH2:22][CH2:21]3)[CH2:19][C@@H:18]2[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[CH3:37])=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:41]>C(OCC)C>[ClH:41].[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([CH2:13][N:14]([CH3:38])[C:15]([N:17]2[CH2:29][CH2:28][C@:20]3([NH:24][C@@H:23]([C:25]([NH2:27])=[O:26])[CH2:22][CH2:21]3)[CH2:19][C@@H:18]2[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[CH3:37])=[O:16])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58169865HCID 58169865, compound

Product 1

HCID 86684790HCID 86684790, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (2R,5S,7R)-N8-{[3,5-bis(trifluoromethyl)phenyl]methyl}-7-(4-fluoro-2-methylphenyl)-N8-methyl-1,8-diazaspiro[4.5]decane-2,8-dicarboxamide (Example 7, 45.5 mg, 0.079 mmol) in Diethyl ether (1 ml) was added 1M HCl in Et2O (0.107 mL, 0.107 mmol) and the resulting mixture was stirred for 30 mins. The solvent was evaporated to give the title compound (40 mg, 0.065 mmol, 82% yield) as a white foam. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.49-9.85 (m, 1H) 8.36-8.60 (m, 1H) 7.96 (s, 1H) 7.92 (br. s., 1H) 7.69 (br. s., 1H) 7.61 (s, 2H) 7.16-7.27 (m, 1H) 6.96 (d, 1H) 6.84 (t, 1H) 4.65 (d, 1H) 4.35 (d, 1H) 4.24-4.32 (m, 1H) 4.20 (dd, 1H) 3.47 (d, 1H) 2.95 (s, 3H) 2.79 (t, 1H) 2.41-2.57 (m, 1H) 2.36 (s, 3H) 1.75-2.23 (m, 7H); HPLC: Rt 4.84 mins (free base); MS: m/z=575 [M+H]+ (free base).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-572a573e31eb44d397ef9c2bba459ffd
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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