Hydrochloric Acid → HCID 86684789, compound

HRID 472706Notes

Reaction equation

HRID 472706 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:39])[C:16]([N:18]2[CH2:30][CH2:29][C@:21]3([NH:25][C@H:24]([C:26]([NH2:28])=[O:27])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[CH3:38])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:42]>C(OCC)C>[ClH:42].[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:39])[C:16]([N:18]2[CH2:30][CH2:29][C@:21]3([NH:25][C@H:24]([C:26]([NH2:28])=[O:27])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[CH3:38])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58169897HCID 58169897, compound

Product 1

HCID 86684789HCID 86684789, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a cold (0° C.) solution of (2S,5S,7R)-N8-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-7-(4-fluoro-2-methylphenyl)-N8-methyl-1,8-diazaspiro[4.5]decane-2,8-dicarboxamide (Example 5, 21 mg, 0.036) in Diethyl ether (1 mL) was added 1N HCl in Diethyl ether (60 μl, 0.060 mmol) and the reaction mixture was stirred for 30 mins. The solvent was evaporated to dryness to give the title compound (23.8 mg, quantitative yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.61-8.07 (m, 5H) 7.11-7.24 (m, 1H) 6.91-6.99 (m, 1H) 6.79-6.90 (m, 1H) 5.23-5.34 (m, 1H) 4.13-4.31 (m, 2H) 3.26-3.47 (m, 1H) 2.79-2.92 (m, 1H) 2.70-2.79 (m, 3H) 1.79-2.66 (m, 11H) 1.38-1.54 (m, 3H). Presence of acid protons in the region between 8.30 and 9.66 ppm.

Workup

  1. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-b1273e5a60b2415d837be3075d37fc37
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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