Water → 6-[3-[[4-(2-Hydroxyethyl)piperazin-1-yl]carbonyl]-benzenesulfonyl]-4-(3-methoxyphenylamino)-8-methylquinoline-3-carboxyamide

HRID 1944913Notes

Reaction equation

HRID 1944913 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)=[CH:20][C:19]([S:32]([C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38](O)=[O:39])(=[O:34])=[O:33])=[CH:18][C:17]=2[CH3:44])(=O)N.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=[CH:60][C:55]=2[N:54]=N1.[OH2:72]>CN(C=O)C>[OH:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][N:4]([C:38]([C:37]2[CH:36]=[C:35]([S:32]([C:19]3[CH:20]=[C:21]4[C:16](=[C:17]([CH3:44])[CH:18]=3)[N:15]=[CH:14][C:13]([CH2:60][C:55]([NH2:54])=[O:72])=[C:22]4[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)(=[O:33])=[O:34])[CH:43]=[CH:42][CH:41]=2)=[O:39])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 76771-(2-Hydroxyethyl)piperazineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 577632883-[[3-(Aminocarbonyl)-4-[(3-methoxyphenyl)amino]-8-methyl-6-quinolinyl]sulfonyl]benzoic acid

Product 1

HCID 1317302966-[3-[[4-(2-Hydroxyethyl)piperazin-1-yl]carbonyl]-benzenesulfonyl]-4-(3-methoxyphenylamino)-8-methylquinoline-3-carboxyamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(piperazin-1-yl)ethanol (160 mg, 1.22 mmol), 3-[3-carbamoyl-4-(3-methoxyphenylamino)-8-methylquinoline-6-sulfonyl]benzoic acid (500 mg, 1.02 mmol), and BOP (540 mg, 1.22 mmol) in 3 mL DMF, TEA (0.34 mL, 3.06 mmol) was added at rt. The reaction mixture was stirred over night. Water was added, and the precipitate was collected by filtration. The filter cake was washed with CH2Cl2, and dried, giving the title compound. ES/MS calcd. for C31H34N5O6S+ 604.2. Found m/z=604.2 (M+H)+.

Workup

  1. additionwas added at rt
  2. filtrationthe precipitate was collected by filtration
  3. washThe filter cake was washed with CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-50c4a210ca3f4ac589854e983df6b698
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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