Ammonia → HCID 18537461, compound

HRID 1058469Notes

Reaction equation

HRID 1058469 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]([C:25]([NH2:27])=[NH:26])[S:20][C:21]=2[S:22][CH2:23]C)[N:16]=1.Br.COC1C=CC(OC)=CC=1NC1SC=C(C2C=C(C(OC)=S)SC=2C)N=1.N>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]([C:25]([NH2:27])=[NH:26])[S:20][C:21]=2[S:22][CH3:23])[N:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 18672219HCID 18672219, compoundHCID 86583829HCID 86583829, compound

Product 1

HCID 18537461HCID 18537461, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-{2-[(2,5-Dimethoxyphenyl)amino](1,3-thiazol-4-yl)}-5-ethylthiothiophene-2-carboxamidine: Methyl 4-{2-[(2,5-dimethoxyphenyl)amino]-(1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide (45.5 mg, 0.09 mmol) was treated as described in Example 154, step (b), followed by preparative thin layer chromatography (500 μm silica gel plate, J. T. Baker, Phillipsburg, N.J., 10%-methanol-CH2Cl2-sat'd. NH3 eluent) to give 9.9 mg (27% yield of 4-{2-[(2,5-dimethoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxamidine. 1H NMR (DMSO-d6, 300 MHz) δ 2.60 (s, 3H), 3.73 (s, 3H), 3.81 (s, 3H), 6.48 (dd, 1H, J=3.1, 8.8 Hz), 6.92 (d, 1H, J=7.9 Hz), 7.05 (s, 1H), 7.5 (bs, 2H), 8.04 (s, 1H), 8.34 (d, 1H, J=1.0 Hz), 9.6 (bs, 1H); Mass Spectrum (ESI) m/z calcd. for C17H18N4O2S3, 406.55 (M+H), found 407.1.

Sources & evidence

ORD record
ord-e469b0c60c4f4140922bece0f6371b4a
Source dataset
uspto-grants-2003_02
Patent number
US06515002B2

Reaction notes

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