HCID 57474462, compound → HCID 178465425, compound

HRID 552959Notes

Reaction equation

HRID 552959 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][CH:14]([N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1.I.CS[C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[NH:31]>C(O)C>[CH2:25]([N:17]([CH:14]1[CH2:13][CH2:12][CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:30]([C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)=[NH:31])[CH:3]=3)[NH:7][CH:6]=2)[CH2:16][CH2:15]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH3:26]

Participants

4

Reactant 2

HCID 57474462HCID 57474462, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178465425HCID 178465425, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 119 (0.4 g, 1.119 mmol) in dry ethanol (20 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.63 g, 2.239 mmol) at room temperature and stirred for 24 h. The solvent was evaporated, diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl, (2×25 mL). The CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude material was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 120 (0.4 g, 60%) as a yellow solid in 2:3 ratio of cis-trans diastereomers. 1H NMR (DMSO-d6) δ 0.98-1.08 (m, 3H), 1.38-1.56 (m, 11H), 1.68-1.85 (m, 4H), 2.05-2.18 (m, 2H), 3.02-3.17 (m, 3H), 3.70-3.76 (m, 1H), 6.31 (brs, 2H), 6.62-6.67 (m, 1H), 6.96-7.01 (m, 1H), 7.09-7.11 (m, 1H), 7.22-7.30 (m, 2H), 7.60 (d, 1H, J=5.1 Hz), 7.70-7.72 (m, 1H), 10.59, 10.62 (2s, 1H); ESI-MS m/z (%): 467 (MH+, 100).

Workup

  1. customThe solvent was evaporated
  2. additiondiluted with sat. NaHCO3 solution (20 mL) and product
  3. extractionwas extracted into CH2Cl, (2×25 mL)
  4. washThe CH2Cl2 layer was washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customcrude material was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-141c50b1b0bb40d1ac796723362d70d6
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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