5-Methylsulfanyl-thiophene-2-carboxamidine → HCID 18536799, compound

HRID 2186629Notes

Reaction equation

HRID 2186629 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([NH2:10])=[NH:9])=[CH:5][CH:4]=1.[CH3:11][CH:12]([C:14]1[CH:15]=[C:16]([NH:20]C2C=C(C(OC)=S)SC=2C)[CH:17]=[CH:18][CH:19]=1)[CH3:13].C[Al](C)C.[NH4+].[Cl-]>>[CH3:11][CH:12]([C:14]1[CH:15]=[C:16]([NH:20][C:4]2[CH:5]=[C:6]([C:8]([NH2:10])=[NH:9])[S:7][C:3]=2[S:2][CH3:1])[CH:17]=[CH:18][CH:19]=1)[CH3:13]

Participants

4

Reactant 3

HCID 103133185-Methylsulfanyl-thiophene-2-carboxamidineHCID 22243074Ammonium chloride trimethylaluminiumHCID 86583853Methyl 4-{[3-(methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxylate

Product 1

HCID 18536799HCID 18536799, compound

Procedure

4-{[3-Methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxamidine: Using a procedure similar to Example 154, step (b), 22.6 mg (0.07 mmol) of methyl 4-{[3-(methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxylate was allowed to react with 8 equiv (0.56 mmol) of the AlMe3/NH4Cl reagent to afford 18.9 mg (78.8%) of) 4-{[3-(methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxamidine. 1H NMR (DMSO-d6, 400 MHz) δ 1.18 (d, 6H, J=9.2 Hz), 2.51 (s, 3H), 2.81 (m, 1H), 6.71-6.77 (m, 2H), 6.85 (s, 1H), 7.14 (m, 1H), 7.98 (s, 1H), 8.32 (s, 1H), 8.88 (bs, 2H), 9.23 (bs, 2H). Mass spectrum (ESI, m/z): Calcd. for C15H19N3S2, 306.11 (M+H), found 306.2.

Sources & evidence

ORD record
ord-62720e1dcf314bedaece7c54b8c4bc9a
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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