Ammonia → HCID 58169902, compound

HRID 472720Notes

Reaction equation

HRID 472720 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:41])[C:16]([N:18]2[CH2:32][CH2:31][C@:21]3([NH:25][C@@:24]([CH3:30])([C:26](OC)=[O:27])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=2[CH3:40])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH3:44]>>[F:10][C:9]([F:11])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]([N:15]([CH3:41])[C:16]([N:18]2[CH2:32][CH2:31][C@:21]3([NH:25][C@@:24]([CH3:30])([C:26]([NH2:44])=[O:27])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=2[CH3:40])=[O:17])[CH3:14])[CH:4]=[C:3]([C:2]([F:43])([F:1])[F:42])[CH:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58169926HCID 58169926, compound2×

Product 1

HCID 58169902HCID 58169902, compoundYield 55.8%

Procedure

In a sealed tube a solution of methyl (2R,5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-2-methyl-1,8-diazaspiro[4.5]decane-2-carboxylate (Intermediate 44, 70 mg, 0.113 mmol) in 7 N methanolic ammonia (5 mL, 35.0 mmol) was shaken at 40° C. for 5 days by PLS. Volatiles were removed in vacuo and the residue was purified by flash chromatography on silica gel using a SNAP 10 g as column and Dichloromethane/Methanol 98:2 as eluent affording the title compound (38 mg, 0.063 mmol, y=55.7%).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel using a SNAP 10 g as column and Dichloromethane/Methanol 98:2 as eluent

Sources & evidence

ORD record
ord-ccf8dc76eba641db9eb97a93360de10b
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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