Diisopropylethylamine → (3-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclopentyl)-carbamic acid tert-butyl ester

HRID 245860

反応式

HRID 245860 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21](O)=[O:22])=[CH:19][N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.Cl.[C:33]([O:37][C:38](=[O:46])[NH:39][CH:40]1[CH2:44][CH2:43][CH:42]([NH2:45])[CH2:41]1)([CH3:36])([CH3:35])[CH3:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>O.CN(C=O)C>[C:33]([O:37][C:38](=[O:46])[NH:39][CH:40]1[CH2:44][CH2:43][CH:42]([NH:45][C:21]([C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([C:6]4[C:5]5[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=5)[N:8]([CH3:11])[N:7]=4)[N:13]=3)[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:19]=2)=[O:22])[CH2:41]1)([CH3:36])([CH3:34])[CH3:35]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45156792tert-Butyl (3-aminocyclopentyl)carbamate--hydrogen chloride (1/1)HCID 712796712-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 1

HCID 71280283(3-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclopentyl)-carbamic acid tert-butyl ester収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A round-bottomed flask was charged with 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (300 mg, 0.66 mmol) and (3-aminocyclopentyl)-carbamic acid tert-butylester hydrochloride (233 mg, 0.98 mmol). DMF (3 ml) was added followed by HATU (274 mg, 0.72 mmol) and N,N-diisopropylethylamine (0.30 ml, 1.72 mmol). The reaction mixture was stirred at room temperature for 30 min. Additional DMF (2 ml) was added and the light yellow suspension was stirred at room temperature overnight. Water was added and the resulting suspension was filtered, washed with water and petroleum ether and dried under high vacuum to afford 413 mg (99%) of (3-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclopentyl)-carbamic acid tert-butyl ester as an off-white powder. The isolated product was determined to be a single diastereomer of unknown relative stereochemistry by NMR analysis.

後処理

  1. stirringthe light yellow suspension was stirred at room temperature overnight
  2. filtrationthe resulting suspension was filtered
  3. washwashed with water and petroleum ether
  4. customdried under high vacuum

出典と根拠

ORDレコード
ord-7261e14f4a4c440e8d97dab208672cd0
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

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