Hydrochloric Acid → HCID 86651618, compound

HRID 384039Notes

Reaction equation

HRID 384039 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-5fc7799b253444dc834776a9751fb83b
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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