Methylamine → HCID 86594248, compound

HRID 1822986Notes

Reaction equation

HRID 1822986 reaction equation
I[CH2:2][CH2:3][C@@H:4]([O:11][C:12]1[C:20]2[S:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:23][NH2:24].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>O1CCCC1.CO>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[S:19]1[C:20]2[C:12]([O:11][C@@H:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:3][CH2:2][NH:24][CH3:23])=[CH:13][CH:14]=[CH:15][C:16]=2[CH:17]=[C:18]1[C:21]#[N:22]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 58630768HCID 58630768, compound

Product 1

HCID 86594248HCID 86594248, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-{[(1R)-3-iodo-1-phenylpropyl]oxy}-1-benzothiophene-2-carbonitrile (156 mg, 0.37 mmol) in tetrahydrofuran (1.5 mL) was added 40% aqueous methylamine (0.5 mL) and the solution was stirred at room temperature for 16 hours. The solvent removed in vacuo and the residue purified by flash chromatography with a gradient of 0–15% methanol in dichloromethane. To a solution of free base (96 mg, 0.3 mmol) in methanol (1 mL) and added a warm solution of fumaric acid (26 mg, 0.3 mmol) in methanol (1 mL). The solvent removed in vacuo, and the solid residue triturated with ether (5 mL), then dried in a vacuum oven at 40° C. for 1 hour to give the title compound (120 mg, 74%); δH (300 MHz, DMSO) 8.40 (1H, s, 3-ArH), 7.61–7.52 (1H, m, ArH), 7.49–7.23 (6H, m, ArH), 7.05–6.98 (1H, m, ArH), 6.45 (2H, s, CHCO2H), 5.85–5.75 (1H, m, CHO), 3.05–2.90 (2H, m, 1-CH2), 2.52 (3H, s, NHCH3) and 2.46–2.07 (2H, m, 2-CH2).

Workup

  1. customThe solvent removed in vacuo
  2. customthe residue purified by flash chromatography with a gradient of 0–15% methanol in dichloromethane
  3. customThe solvent removed in vacuo
  4. customthe solid residue triturated with ether (5 mL)
  5. customdried in a vacuum oven at 40° C. for 1 hour

Sources & evidence

ORD record
ord-e8ba9a057beb4a3e9c94e885c330ce2b
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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