1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl {2-[(3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoyl)amino]ethyl}carbamate

HRID 875494ノート

反応式

HRID 875494 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:27])[C:10]=1[C:11]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[C:17]([C:22]([CH:24]3[CH2:26][CH2:25]3)=[O:23])[C:16]=2[CH:15]=[CH:14]1)=[O:12])[C:5]([OH:7])=O.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:27])[C:10]=1[C:11]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[C:17]([C:22]([CH:24]3[CH2:25][CH2:26]3)=[O:23])[C:16]=2[CH:15]=[CH:14]1)=[O:12])[C:5]([NH:49][CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:57])([CH3:56])[CH3:58])=[O:7]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 710615703,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoic acid

生成物 1

HCID 86720668tert-butyl {2-[(3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoyl)amino]ethyl}carbamate収率 35.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To the stirred mixture of 3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoic acid (50 mg, 0.119 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (26.8 mg, 0.14 mmol) and 1-hydroxybenzotriazole (19 mg, 0.14 mmol) in N,N-dimethylformamide, was added tert-butyl (2-aminoethyl)carbamate (19 mg, 0.119 mmol). The reaction mixture was stirred at room temperature for about 16 hours. The reaction mixture was poured drop wise into cold saturated solution of sodium bicarbonate. The precipitated solid was filtered, washed with water and dried. Purification by preparative thin layer chromatography (2% methanol and dichloromethane as eluent) afforded tert-butyl {2-[(3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoyl)amino]ethyl}carbamate (23 mg, 35%).

後処理

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried
  4. customPurification by preparative thin layer chromatography (2% methanol and dichloromethane as eluent)

出典と根拠

ORDレコード
ord-7dd45f0d74ff4ee0bda8f6f78595ef3d
出典データセット
uspto-grants-2015_03
特許番号
US08980911B2

反応ノート

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