(quinolin-3-yl)thiourea → HCID 18536962, compound

HRID 412973Notes

Reaction equation

HRID 412973 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12]1[N:13]=[C:14]([NH:17][C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:15][CH:16]=1.[Br:28]CC(C1C=C(C(OC)=S)SC=1C)=O.NC(NC1C=NC2C(C=1)=CC=CC=2)=S>>[BrH:28].[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12]1[N:13]=[C:14]([NH:17][C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:15][CH:16]=1

Participants

4

Reactant 3

HCID 1480927(quinolin-3-yl)thioureaHCID 18536963Methyl 5-methylthio-4-[2-(3-quinolylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxylateHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 18536962HCID 18536962, compoundYield 78%

Procedure

Methyl 5-methylthio-4-[2-(3-quinolylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxylate: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (90 mg, 0.28 mmol) was allowed to react with amino(3-quinolylamino)methane-1-thione (59.1 mg) as described in Example 154, step (a) to give 107.5 mg (78% yield) of methyl 5-methylthio-4-[2-(3-quinolylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.75 (s, 3H), 3.84 (s, 3H), 7.52 (s, 1H), 7.92-8.05 (m, 2H), 8.22 (s, 1H), 9.22 (m, 2H); Mass Spectrun (ESI) m/z calcd. for C19H15N3O2S3, 413.54 (M+H), found 414.1.

Sources & evidence

ORD record
ord-3ee2a2b6b51947d69526f9ab4fd4894e
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

Loading…