Water → HCID 57500666, compound

HRID 1919652Notes

Reaction equation

HRID 1919652 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[CH:18]=[CH:19][S:20][C:16]=3[C:15]3[CH:14]=[CH:13][C:12]([C:21]([OH:23])=O)=[CH:11][C:10]=3[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26].CCN=C=NCCCN(C)C.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:24][S:25]([NH:28][C:21]([C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[S:20][CH:19]=[CH:18][C:17]=3[C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:9][C:10]=2[CH:11]=1)=[O:23])(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 50941860HCID 50941860, compound

Product 1

HCID 57500666HCID 57500666, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(phenylamino)thieno[3,2-c]quinoline-7-carboxylic acid (6 mg) was reacted with methyl sulfonamide (120 mg), EDCI (80 mg) and DMAP (20 mg) in anhydrous DMF (0.5 ml). After 5 hours, water was added and the solution subjected to preparative HPLC. Genevac evaporation provided N-(methylsulfonyl)-4-(phenylamino)thieno[3,2-c]quinoline-7-carboxamide as a solid (6 mg, 81% yield). LCMS (ES): 95% pure, m/z 398 [M+1]+.

Workup

  1. customGenevac evaporation

Sources & evidence

ORD record
ord-ffd762e40fad45d4a9cf0754bcd7e712
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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