Pyridine → N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 2098375

Reaction equation

HRID 2098375 reaction equation
C(C1C=C([NH:11][C:12]([C:14]2(C)[CH2:19][CH2:18][N:17]([C:20](OC(C)(C)C)=O)C[CH2:15]2)=O)C=CC=1)(C)(C)C.C(O[C:33]([N:35]1[CH2:40][CH2:39][C:38]([CH3:44])([C:41]([OH:43])=O)[CH2:37][CH2:36]1)=O)(C)(C)C.[N:45]1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[C:57]([C:61]1[CH:62]=[C:63]([CH:65]=[CH:66][CH:67]=1)[NH2:64])([CH3:60])([CH3:59])[CH3:58]>CN(C=O)C.ClC(Cl)C.ClCCl>[C:57]([C:61]1[CH:62]=[C:63]([NH:64][C:41]([C:38]2([CH3:44])[CH2:37][CH2:36][N:35]([C:33]3[C:19]4[C:14]([CH3:15])=[CH:12][NH:11][C:18]=4[N:17]=[CH:20][N:45]=3)[CH2:40][CH2:39]2)=[O:43])[CH:65]=[CH:66][CH:67]=1)([CH3:60])([CH3:58])[CH3:59]

Participants

9

Reactant 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 793343-tert-ButylanilineHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 86635224HCID 86635224, compound

Product 1

HCID 57920200N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideYield 61%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Preparation of tert-Butyl 4-(3-tert-butylphenylcarbamoyl)-4-methylpiperidine-1-carboxylate. To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.30 g, 1.2 mmol), DMF (20 drops), and pyridine (0.38 g, 4.8 mmol) in dichloroethane (10 mL) was added oxalyl chloride (0.15 g, 1.2 mmol). The mixture was stirred for 40 minutes, and 3-tert-butylaniline was added. The mixture was stirred for 1 hour, diluted with dichloromethane, washed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl, dried over MgSO4, and concentrated. Silica gel chromatography (0-2% MeOH:CH2Cl2) gave the title compound in 61% yield. MS (ES+) [M+H]+375.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. washwashed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ed7a01bbd0af4d918e25666e97d4466e
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Linked notes

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