Triethylamine → 3-(Benzenesulfonyl-benzyl-amino)-N-(1H-indazol-6-yl)-benzamide

HRID 62819

反応式

HRID 62819 の反応式
[C:1]1([S:7]([N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:27][C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[N:33][NH:34]2)=[CH:30][CH:29]=1.Cl.CN(C)CCCN=C=NCC.SC1SC2C=CC=CC=2N=1.C(N(CC)CC)C>C(#N)C>[C:1]1([S:7]([N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:27][C:28]2[CH:36]=[C:35]3[C:31]([CH:32]=[N:33][NH:34]3)=[CH:30][CH:29]=2)=[O:16])(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 814231H-Indazol-6-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673109503-(Benzenesulfonyl-benzyl-amino)-benzoic acidHCID 178418395HCID 178418395、化合物

生成物 1

HCID 461825053-(Benzenesulfonyl-benzyl-amino)-N-(1H-indazol-6-yl)-benzamide収率 45.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 3-(benzenesulfonyl-benzyl-amino)-benzoic acid (25 mg, 0.068 mmol), 6-amino-1H-indazole (18 mg, 0.136 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (15 mg, 0.075 mmol), mercaptobenzothiazole (2 mg, 0.007 mmol) and triethylamine (24 μl, 0.17 mmol) in dry acetonitrile (2 ml) were stirred at room temperature for 15 hrs. The reaction mixture was quenched with water (10 ml) and extracted with dichloromethane (3×7 ml). The organics were combined, dried (PTFE frit) and concentrated in vacuo. The crude residue was purified by preparative TLC (10% diethyl ether in dichloromethane) to afford the title compound as a brown solid (15 mg, 45%). HPLC retention time 5.80 min. Mass spectrum (ES+) m/z 483 (M+H).

後処理

  1. customThe reaction mixture was quenched with water (10 ml)
  2. extractionextracted with dichloromethane (3×7 ml)
  3. dry with materialdried (PTFE frit)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative TLC (10% diethyl ether in dichloromethane)

出典と根拠

ORDレコード
ord-e00d585c5899472b8e024f7de6bf0a1a
出典データセット
uspto-grants-2016_09
特許番号
US09447033B2

関連ノート

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