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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoyl]piperidine-4-carbonitrile

HRID 1517536
Notes
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Reaction equation

HRID 1517536 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([O:28][CH3:29])=[CH:20][C:16]=2[C:17]([OH:19])=O)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)#N.C1C=CC2N(O)N=[N:44][C:42]=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([O:28][CH3:29])=[CH:20][C:16]=2[C:17]([N:32]2[CH2:33][CH2:34][CH:35]([C:42]#[N:44])[CH2:36][CH2:37]2)=[O:19])=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 73736PiperidinocarbonitrileHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 673744112-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid

Product 1

HCID 67374249
1-[2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoyl]piperidine-4-carbonitrile
Yield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 4—To a solution of 68 (100 mg, 0.26 mmol) in DMF (3 mL) were added 4 cyano-piperidine (32 mg, 0.29 mmol), HOBt (39 mg, 0.29 mmol), EDCI (56 mg, 0.29 mmol) and DIPEA. The reaction mixture was stirred at RT overnight then quenched with H2O and thrice extracted with EtOAc. The combined extracts were sequentially washed with H2O (3 times) and brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford 126 mg (99%) of 1-[2-(2-benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoyl]piperidine-4-carbonitrile (70) as a pale yellow foam.

Workup

  1. customthen quenched with H2O and thrice
  2. extractionextracted with EtOAc
  3. washThe combined extracts were sequentially washed with H2O (3 times) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58e11924eb374a5a96a06756f90e6b75
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232271B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes