Water → HCID 67491554, compound

HRID 1028441Notes

Reaction equation

HRID 1028441 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[C:9]([O:49][CH3:50])=[C:10]([NH:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([CH3:48])=[C:25]([CH:47]=2)[O:26][C:27]2[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][CH:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]3)[CH:28]=2)=[O:20])[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1.C(N(CC)CC)C.O>ClCCl>[C:14]([C:12]1[CH:13]=[C:8]([NH:7][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])[C:9]([O:49][CH3:50])=[C:10]([NH:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([CH3:48])=[C:25]([CH:47]=2)[O:26][C:27]2[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][CH:34]3[CH2:35][CH2:36][N:37]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:38][CH2:39]3)[CH:28]=2)=[O:20])[CH:11]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 67491683HCID 67491683, compound

Product 1

HCID 67491554HCID 67491554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At ambient temperature 36 μl cyclopropanecarboxylic acid chloride are added to a solution of 160 mg tert-butyl 4-{4-[5-(3-amino-5-tert-butyl-2-methoxy-phenylcarbamoyl)-2-methyl-phenoxy]-pyridin-2-ylmethyl}-piperidine-1-carboxylate and 70 μl triethylamine in 2 ml dichloromethane. The solution is stirred overnight at ambient temperature and then mixed with water. The mixture is extracted with dichloromethane, and the combined extracts are washed with water and saturated aqueous saline solution, dried (MgSO4) and evaporated down. The residue is chromatographed on silica gel with cyclohexane/ethyl acetate (50:500:100) as eluant.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe combined extracts are washed with water and saturated aqueous saline solution
  3. dry with materialdried (MgSO4)
  4. customevaporated down
  5. customThe residue is chromatographed on silica gel with cyclohexane/ethyl acetate (50:500:100) as eluant

Sources & evidence

ORD record
ord-1c2255daa161445c824bce759c5d9e16
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

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