Hydrochloric Acid → HCID 86651618, compound

HRID 472710Notes

Reaction equation

HRID 472710 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 58169909HCID 58169909, compound

Product 1

HCID 86651618HCID 86651618, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (2S,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 9, 66 mg, 0.115 mmol) in Diethyl ether (1 ml) was added 1M HCl in Et2O (0.2 ml, 0.200 mmol) and the resulting mixture was stirred for 30 mins. The solvent was evaporated to dryness to give the title compound (61.7 mg, 0.101 mmol, 88% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.50-9.86 (m, 1H) 8.25-8.50 (m, 1H) 7.87-8.01 (m, 2H) 7.67 (s, 1H) 7.60 (s, 2H) 7.20-7.29 (m, 1H) 6.90-7.00 (m, 1H) 6.80-6.90 (m, 1H) 4.58-4.70 (m, 1H) 4.31-4.43 (m, 1H) 4.13-4.30 (m, 2H) 3.42-3.54 (m, 1H) 2.95 (s, 3H) 2.75-2.88 (m, 1H) 1.74-2.67 (m, 11H). HPLC: Rt=4.82 mins (free base); MS: m/z=575 [M+H]+ and 597 [M+Na]+ (free base).

Workup

  1. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-f55653b8a47544b5bed813922e6b9aaa
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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