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

HRID 2098375

反応式

HRID 2098375 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed7a01bbd0af4d918e25666e97d4466e
出典データセット
uspto-grants-2013_05
特許番号
US08450332B2

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