Tris(hydroxymethyl)aminomethane → 1-[3-(aminosulfonyl)phenyl]-8-[(2-chlorobenzoyl)amino]-1H-benzo[g]indazole-3-carboxamide

HRID 22984

Reaction equation

HRID 22984 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([N:11]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:14]=4)[N:10]=[C:9]3[C:23]([NH2:25])=[O:24])=[C:4]2[CH:3]=1.[Cl:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32].C(O)C(N)(CO)CO>N1C=CC=CC=1>[NH2:22][S:19]([C:15]1[CH:14]=[C:13]([N:11]2[C:12]3[C:8](=[CH:7][CH:6]=[C:5]4[CH:26]=[CH:27][C:2]([NH:1][C:31](=[O:32])[C:30]5[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=5[Cl:28])=[CH:3][C:4]4=3)[C:9]([C:23]([NH2:25])=[O:24])=[N:10]2)[CH:18]=[CH:17][CH:16]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 691102-Chlorobenzoyl chlorideHCID 225925238-amino-1-[3-(aminosulfonyl)phenyl]-1H-benzo[g]indazole-3-carboxamide

Product 1

HCID 102081801-[3-(aminosulfonyl)phenyl]-8-[(2-chlorobenzoyl)amino]-1H-benzo[g]indazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 8-amino-1-[3-(aminosulfonyl)phenyl]-1H-benzo[g]indazole-3-carboxamide from step 2 (76.2 mg, 0.20 mmol) in pyridine (25 mL) at RT was added 2-chlorobenzoic chloride (53 mg, 0.3 mmol). After 14 h, trisamine was added and the mixture was stirred for 2 h. The mixture was filtered through a silica gel pad with EtOAc and concentrated. The resulting title product was a solid (42 mg, 40%). Its structure was confirmed by 1H NMR and MS (521, M+1). C25H18ClN5O4S, Calc.: C: 57.75, H: 3.49; N: 13.47; Found, C: 57.06, H: 3.65, N: 13.51.

Workup

  1. filtrationThe mixture was filtered through a silica gel pad with EtOAc
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5f7de2e00e384a6b8a93e23288a961eb
Source dataset
uspto-grants-2005_02
Patent number
US06849653B2

Linked notes

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