HCID 59807144, compound → HCID 178452053, compound

HRID 1922482Notes

Reaction equation

HRID 1922482 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3[CH:21]=[C:22]([NH2:25])[CH:23]=[CH:24][C:15]2=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32](SC)=[NH:33]>C(O)C.C(=O)(O)[O-].[Na+]>[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32](=[NH:33])[NH:25][C:22]1[CH:23]=[CH:24][C:15]2[N:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]3)[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:21]=1

Participants

5

Reactant 2

HCID 59807144HCID 59807144, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178452053HCID 178452053, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 4 (0.6586 g, 1.906 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (1.087 g, 3.812 mmol) at room temperature and was stirred for 3 hours. The mixture was diluted with saturated sodium bicarbonate solution (50 mL) and was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL) and dried (Na2SO4). The concentrated crude product was subject to flash chromatography on silica gel using 2.5-5% MeOH/CH2Cl2, which resulted in a brown foam, compound 5 (0.42 g, 48%). 1H NMR (CDCl3) δ 7.42-7.40 (m, 2H), 7.08-7.05 (t, J=9.0 Hz, 1H), 6.92 (d, J=8.1 Hz, 1H), 6.77-6.73 (m, 2H), 4.13-4.09 (m, 2H), 3.37 (tt, J=7.2, 21.9 Hz, 1H), 2.95-2.71 (m, 6H), 1.87 (d, J=12.9 Hz, 2H), 1.77-1.53 (m, 7H), 1.47 (s, 9H); MS-ESI (m/z, %): 457 (MH+, 14), 455 (M+, 100), 219 (18).

Workup

  1. extractionwas extracted with CH2Cl2 (100 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationThe concentrated crude product

Sources & evidence

ORD record
ord-df796bf117644cc6aaea74b9e547a285
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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