Water → HCID 178484891, compound

HRID 1597099Notes

Reaction equation

HRID 1597099 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([NH2:10])=[NH:9])=[CH:5][C:4]=1[C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1.[CH3:22]N.O>CO>[NH:9]=[C:8]([NH:10][CH3:22])[C:6]1[S:7][C:3]([S:2][CH3:1])=[C:4]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 18536889HCID 18536889, compound

Product 1

HCID 178484891HCID 178484891, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-Methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxamidine (20 mg, 0.06 mmol) as prepared in Example 10 step (b) was dissolved in MeOH, and to this solution methylamine (0.6 mL, 2M solution in tetrahydrofuran) was added. This solution was refluxed for 6 h, at which time the solvents were removed under vacuum to give a solid. This solid was dissolved in a small amount of MeOH. H2O was added dropwise to the methanolic solution until a precipitate was formed. This solid was isolated, washed with a small amount of water and dried under vacuum to give 15 mg (72%) of {imino[5-methylthio-4-(4-phenyl(1,3-thiazol-2-yl))(2-thienyl)]methyl}methylamine. 1H-NMR (DMSO-d6; 300 MHz) δ 2.77 (s, 3H), 3.00 (s, 3H), 7.36-7.42 (m, 1H), 7.47-7.52 (m, 2H), 8.07-8.10 (m, 2H), 8.23 (s, 1H), 8.55 (s, 1H). Mass spectrum (ESI, m/z): Calcd. for C16H15N3S3, 346.5 (M+H), found 346.2.

Workup

  1. temperatureThis solution was refluxed for 6 h, at which time the solvents
  2. customwere removed under vacuum
  3. customto give a solid
  4. customwas formed
  5. customThis solid was isolated
  6. washwashed with a small amount of water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9995075dc3394dd1a67851b27c39a5fd
Source dataset
uspto-grants-2001_09
Patent number
US06291514B1

Reaction notes

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