Hydrochloric Acid → HCID 86651619, compound

HRID 384040Notes

Reaction equation

HRID 384040 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 58169853HCID 58169853, compound

Product 1

HCID 86651619HCID 86651619, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (2R,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 11, 54 mg, 0.092 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 (57.4 mg, 0.091 mmol, 99% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.35-9.68 (m, 1H) 8.35-8.60 (m, 1H) 7.95 (s, 1H) 7.90 (br. s., 1H) 7.70 (br. s., 1H) 7.56 (s, 2H) 7.11-7.25 (m, 1H) 6.94 (d, 1H) 6.80 (t, 1H) 5.28-5.39 (m, 1H) 4.13-4.35 (m, 2H) 3.44 (d, 1H) 2.85 (s, 3H) 2.77 (t, 1H) 2.40-2.59 (m, 1H) 2.35 (s, 3H) 1.75-2.21 (m, 7H) 1.50 (d, 3H); HPLC: Rt=4.95 mins (free base); MS: m/z=589 [M+H]+ (free base)

Workup

  1. customThen the solvent was evaporated to dryness

Sources & evidence

ORD record
ord-47e415eaab7b4533bd27f7a02f1ec101
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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