HCID 18536940, compound → HCID 86758684, compound

HRID 2298661Notes

Reaction equation

HRID 2298661 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=1[CH3:10])=O.[NH2:15][C:16]([NH:18][C:19]1[CH:31]=[CH:30][C:29]2[C:28]3[C:23](=[CH:24][C:25]([Br:32])=[CH:26][CH:27]=3)[CH2:22][C:21]=2[CH:20]=1)=[S:17]>>[BrH:1].[Br:32][C:25]1[CH:24]=[C:23]2[C:28]([C:29]3[CH:30]=[CH:31][C:19]([NH:18][C:16]4[S:17][CH:2]=[C:3]([C:5]5[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=5[CH3:10])[N:15]=4)=[CH:20][C:21]=3[CH2:22]2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 18536940HCID 18536940, compoundHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758684HCID 86758684, compoundYield 84.7%

Procedure

Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (90 mg, 0.28 mmol) was allowed to react with amino[(7-bromofluoren-2-yl)amino]methane-1-thione (92.8 mg) as described in Example 154, step (a) to give 141 mg (82% yield) of methyl 4-{2-[(7-bromofluoren-2-yl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ2.70 (s, 3H), 3.83 (s, 3H), 3.93 (s, 2H), 7.33 (s, 1H), 7.51 (dd, 1H, J=1.9, 8.0 Hz), 7.65 (dd, 1H, J=2.0, 8.4 Hz), 7.74 (ad, 2H, J=8.3 Hz), 7.83 (ad, 1H, J=8.4 Hz), 8.18 (s, 1H), 8.23 (d, 1H, J=1.4 Hz), 10.47 (s, 1H).

Sources & evidence

ORD record
ord-c64cb0ae939b486580e14cd50b29f4ab
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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