Tris(hydroxymethyl)aminomethane → HCID 22291576, compound

HRID 457302Notes

Reaction equation

HRID 457302 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]2[CH2:6][CH2:7][C:8]3[C:9]([C:25]([NH2:27])=[O:26])=[N:10][N:11]([C:13]4[CH:18]=[CH:17][C:16]([S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])=[CH:15][CH:14]=4)[C:12]=3[C:4]=2[CH:3]=1.[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34].C(O)C(N)(CO)CO.CCOC(C)=O>N1C=CC=CC=1>[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH:1][C:2]1[CH:29]=[CH:28][C:5]2[CH2:6][CH2:7][C:8]3[C:9]([C:25]([NH2:27])=[O:26])=[N:10][N:11]([C:13]4[CH:14]=[CH:15][C:16]([S:19]([N:22]([CH3:23])[CH3:24])(=[O:20])=[O:21])=[CH:17][CH:18]=4)[C:12]=3[C:4]=2[CH:3]=1)=[O:34]

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8857Ethyl AcetateHCID 691102-Chlorobenzoyl chlorideHCID 10158540HCID 10158540, compound

Product 1

HCID 22291576HCID 22291576, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 8-amino-1-{4-[(dimethylamino)sulfonyl]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (Example 46) (1.52 g, 3.70 mmol) in pyridine (25 mL) at RT was added 2-chlorobenzoic chloride (970 mg, 5.55 mmol). After 14 h, trisamine (1 g) was added and the mixture was stirred for 2 h. The mixture was filtered through a silica gel pad with EtOAc and concentrated. Column chromatography (silica gel, EtOAc) gave the title compound as a yellow solid (900 mg, 1.63 mmol, 44%). Its structure was confirmed by 1H NMR and MS (551, M+1). C27H24ClN5O4S, Calc.: C: 58.96; H: 4.40, N: 12.73; Found, C: 58.66; H: 4.65, N: 12.58.

Workup

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

Sources & evidence

ORD record
ord-8b47dd9c4634451c8b4e8ca93a41c3dc
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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