Hydrochloric Acid → HCID 86684790, compound

HRID 384037Notes

Reaction equation

HRID 384037 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., 1 H) 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, 1 H) 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-1aaf2f87486842539365f8a7745e96fb
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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