Hydrochloric Acid → HCID 86684789, compound

HRID 384035Notes

Reaction equation

HRID 384035 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, 1 H) 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-3ecbac79177440b294a96fe05b486339
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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