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

HRID 2098375

반응식

HRID 2098375 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ed7a01bbd0af4d918e25666e97d4466e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450332B2

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