Diisopropylethylamine → 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

HRID 1850548ノート

反応式

HRID 1850548 の反応式
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=C[CH:44]=[CH:45][C:40]=2N=N1.[CH:54](N(CC)C(C)C)(C)C.[CH:63]12[N:70]([C:71]([OH:73])=[O:72])[CH:67]([CH2:68][CH2:69]1)[CH2:66][NH:65][CH2:64]2>CN(C=O)C.CCOC(C)=O>[C:45]([O:72][C:71]([N:70]1[CH:63]2[CH2:69][CH2:68][CH:67]1[CH2:66][N:65]([C:20]([C:19]1[CH:18]=[N:17][C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[CH:8]=[C:7]([C:25](=[O:29])[N:26]([CH3:27])[CH3:28])[N:6]([CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)[C:10]=4[N:11]=3)=[CH:24][CH:23]=1)=[O:22])[CH2:64]2)=[O:73])([CH3:44])([CH3:40])[CH3:54]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222733513,8-Diaza-bicyclo[3.2.1]octane-8-carboxylic acidHCID 583154726-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid

生成物 1

HCID 673560653-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid (400 mg, 1.01 mmol) in DMF (5 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU, 580 mg, 1.53 mmol, 1.5 equiv) and N,N-diisopropylethylamine (0.55 mL, 3.0 equiv) and the resulting mixture stirred at room temperature for 5 minutes. To the reaction mixture was added 3,8-Diaza-bicyclo[3.2.1]octane-8-carboxylic acid Pert-butyl ester (250 mg, 1.18 mmol. 1.1 eq). The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted in EtOAc, washed with 0.5M HCl, water, dried over Na2SO4, filtered and concentrated. Material was immediately used in next step without further purification. MS: (M+H)=589.7

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. washwashed with 0.5M HCl, water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customMaterial was immediately used in next step without further purification

出典と根拠

ORDレコード
ord-bf157198fe7748929b642636dddef7c1
出典データセット
uspto-grants-2015_02
特許番号
US08957074B2

反応ノート

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