Triethylamine → (R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridine-5-carboxylate

HRID 79516ノート

反応式

HRID 79516 の反応式
[N:1]1([C:7]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=[C:9]3[NH:17][CH:18]=[CH:19][C:8]=23)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:20]([O:24][C:25]([NH:27][C@H:28]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:29](O)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl>[C:20]([O:24][C:25]([NH:27][C@H:28]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:29]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=[C:9]3[NH:17][CH:18]=[CH:19][C:8]=23)[CH2:6][CH2:5]1)=[O:30])=[O:26])([CH3:23])([CH3:21])[CH3:22]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 68762011methyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

生成物 1

HCID 68765221(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridine-5-carboxylate収率 29.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl 4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.23 g, 0.69 mmol) and (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.227 g, 0.759 mmol) were placed in DCM (5 mL) at room temperature. HOBT-H2O (0.147 g, 0.966 mmol), EDCI (0.172 g, 0.897 mmol) and triethylamine (0.48 mL, 3.45 mmol) were then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude residue. The residue was purified by column chromatography (500:7 DCM:MeOH) to give (R)-methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.11 g, 29.4% yield).

後処理

  1. customThe reaction was then quenched with saturated Na2CO3
  2. extractionextracted with DCM
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue
  7. customThe residue was purified by column chromatography (500:7 DCM:MeOH)

出典と根拠

ORDレコード
ord-0f0cfbb3cb3e48468f0960affb63a006
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

反応ノート

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