Hydrochloric Acid → HCID 86651620, compound

HRID 384041Notes

Reaction equation

HRID 384041 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 58169859HCID 58169859, compound

Product 1

HCID 86651620HCID 86651620, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (2S,5S,7R)—N8-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-7-(4-fluoro-2-methylphenyl)-N8-methyl-1,8-diazaspiro[4.5]decane-2,8-dicarboxamide (Example 13, 67 mg, 0.113 mmol) in Diethyl ether (1 ml) was added 1M HCl in Et2O (200 μl, 0.200 mmol) and the resulting mixture was stirred for 30 mins. Then the solvent was evaporated to dryness to give the title compound (68.2 mg, 0.109 mmol, 96% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.67 (br. s., 1H) 8.34 (br. s., 1H) 7.87-8.00 (m, 2H) 7.66 (s, 1H) 7.55 (s, 2H) 7.13-7.32 (m, 1H) 6.94 (d, 1H) 6.76-6.89 (m, 1H) 5.25-5.43 (m, 1H) 4.07-4.38 (m, 2H) 3.40-3.51 (m, 1H) 2.84 (s, 3H) 2.71-2.91 (m, 1H) 2.33 (s, 3H) 1.78-2.58 (m, 8H) 1.50 (d, 3H); HPLC: Rt=4.93 mins (free base); MS: peak @ m/z=589 [M+H]+ and 611 [M+Na]+ (free base).

Workup

  1. customThen the solvent was evaporated to dryness

Sources & evidence

ORD record
ord-3d87579d525148dfa33b5cedc556e8f5
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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