Ammonium Chloride → 4-(2-Amino-6-phenoxy-quinolin-3-yl)-N-cyclohexyl-N-methyl-4-(tetrahydro-pyran-4-yl)-butyramide

HRID 502866Notes

Reaction equation

HRID 502866 reaction equation
[CH:1]1([N:7]([CH3:39])[C:8](=[O:38])[CH2:9][CH2:10][CH:11]([CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[C:12]([C:30]#[N:31])=[CH:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=[CH:16][C:15]=2[N+:27]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+].[Cl-]>CO.[Zn]>[NH2:31][C:30]1[C:12]([CH:11]([CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH2:10][CH2:9][C:8]([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:39])=[O:38])=[CH:13][C:14]2[C:15](=[CH:16][CH:17]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=2)[N:27]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 672693405-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid cyclohexyl-methyl-amide

Product 1

HCID 574062904-(2-Amino-6-phenoxy-quinolin-3-yl)-N-cyclohexyl-N-methyl-4-(tetrahydro-pyran-4-yl)-butyramide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid cyclohexyl-methyl-amide (0.37 g, 0.697 mmol) in methanol was divided evenly into two microwave tubes containing Zn (0.9 g, 13.8 mmol) and NH4Cl (0.1 g, 1.87 mmol). The reaction mixture was subjected to μW at 95° C. for 900 sec. The reaction mixture was filtered through Celite®, and the filtrate was evaporated in vacuo to yield a crude product which was purified on a silica gel column (10% MeOH/dichloromethane) to yield the title compound as a residue.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customthe filtrate was evaporated in vacuo
  3. customto yield a crude product which
  4. customwas purified on a silica gel column (10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-70ab8d6c3e484fa98b6342397eeaef88
Source dataset
uspto-grants-2010_08
Patent number
US07776882B2

Reaction notes

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