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

HRID 62819

반응식

HRID 62819 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e00d585c5899472b8e024f7de6bf0a1a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447033B2

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