N-Methylcyclohexylamine → HCID 70571424, compound

HRID 2403578Notes

Reaction equation

HRID 2403578 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=O)[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH:38]1([N:37]([CH3:36])[C:33]([CH:30]2[CH2:29][CH2:28][N:27]([C:24]3[N:23]=[CH:22][C:21]([C:17]4[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=4)[CH2:14][N:12]([CH3:13])[C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:26][N:25]=3)[CH2:32][CH2:31]2)=[O:35])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68106387HCID 68106387, compound

Product 1

HCID 70571424HCID 70571424, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{5-[3-({[N-(tert-Butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperidine-4-carboxylic acid (200 mg) and N-methylcyclohexanamine (94 mg) were suspended in methylene chloride (4 ml), and WSC hydrochloride (159 mg) and HOBt (112 mg) were added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was subjected to liquid separation with CHCl3 and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, and then the aqueous layer was extracted with CHCl3 again. These organic layers were combined and dried over Na2SO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (0% to 5% MeOH/CHCl3) to obtain tert-butyl (2-{[3-(2-{4-[cyclohexyl(methyl)carbamoyl]piperidin-1-yl}pyrimidin-5-yl)benzyl](methyl)amino}-2-oxoethyl)carbamate (169 mg).

Workup

  1. customThe reaction mixture was subjected to liquid separation with CHCl3
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CHCl3 again
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (0% to 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-f6a294d27c5442c8ad360ea3fbee2461
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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