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

HRID 1186261

Reaction equation

HRID 1186261 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c60bbf31b8c34f67bdea69ebb0b79f5b
Source dataset
uspto-grants-2014_03
Patent number
US08673901B2

Linked notes

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