Methanol → HCID 86604273, compound

HRID 2054172Notes

Reaction equation

HRID 2054172 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[CH:24]=[C:25]([NH2:30])[CH:26]=[CH:27][C:28]=4[CH3:29])[CH2:19][CH2:18]3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[C:31]([O:35][N:36]([CH2:40][C:41](O)=[O:42])[C:37]([CH3:39])=[O:38])([CH3:34])([CH3:33])[CH3:32].Cl.CN(C)CCCN=C=NCC.CO>C(Cl)Cl.CN(C)C=O.CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:31]([O:35][N:36]([CH2:40][C:41]([NH:30][C:25]1[CH:26]=[CH:27][C:28]([CH3:29])=[C:23]([CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][C:13]3[CH:12]=[CH:11][C:10]([S:9][C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[CH:15][CH:14]=3)[CH2:18][CH2:19]2)[CH:24]=1)=[O:42])[C:37]([CH3:39])=[O:38])([CH3:34])([CH3:33])[CH3:32]

Participants

8

Reactant 4

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22142721HCID 22142721, compoundHCID 24990093HCID 24990093, compound

Product 1

HCID 86604273HCID 86604273, compoundYield 50.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a stirred solution of 3-(1-{[4-(4-methoxyphenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenylamine (121 mg, 0.289 mmol) in CH2Cl2/dimethylformamide (2.00/0.200 mL) was added 2-[(tert-butoxy)-N-methylcarbonylamino]acetic acid (54.6 mg, 0.289 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (111 mg, 0.578 mmol) and 4-dimethylaminopyridine (5.00 mg). The reaction mixture was stirred at room temperature for 10 h, then partitioned between CH2Cl2 (10 mL) and saturated NaHCO3 solution (10 mL) and the organic phase was separated and washed with water (10 mL), then brine (10 mL), dried over MgSO4 and concentrated in vacuo to give the crude product. Purification by flash column chromatography (eluent: CH2Cl2 then 3% methanol in CH2Cl2) gave 2-[(tert-butoxy)-N-methylcarbonylamino]-N-[3-(1-{[4-(4-methoxyphenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenyl]acetamide (84.7 mg, 50.1% yield) as a yellow solid.

Workup

  1. custompartitioned between CH2Cl2 (10 mL) and saturated NaHCO3 solution (10 mL)
  2. customthe organic phase was separated
  3. washwashed with water (10 mL)
  4. dry with materialbrine (10 mL), dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customPurification by flash column chromatography (eluent

Sources & evidence

ORD record
ord-e26b732defb34f198ed01b6a603cb546
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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