Methyl chloroformate → HCID 59656635, compound

HRID 2054919Notes

Reaction equation

HRID 2054919 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:12][C:11]([CH2:21][CH2:22][NH2:23])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].C(N(CC)CC)C.[CH3:31][O:32][C:33](Cl)=[O:34]>CN(C=O)C>[CH3:31][O:32][C:33](=[O:34])[NH:23][CH2:22][CH2:21][C:11]1[CH:12]=[C:13]([O:14][CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[C:3]2[C:2]([NH2:1])=[C:6]([C:7](=[O:8])[NH2:9])[S:5][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 11450439HCID 11450439, compound

Product 1

HCID 59656635HCID 59656635, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-amino-6-(2-amino-ethyl)-4-cyclopentylmethoxy-benzo[b]thiophene-2-carboxylic acid amide (11) (HCl salt form, 0.050 g, 0.14 mmol) and triethylamine (0.07 mL, 0.5 mmol) in DMF (1 mL) at 0° C. was added methyl-chloroformate (0.02 mL, 0.3 mmol). The reaction was allowed to warm to room temperature and stirred for 1 h. The reaction was quenched with MeOH and the solvent was removed under reduced pressure. The residue was purified by flash silica gel chromatography to afford the title compound (0.025 g, 47%).

Workup

  1. customThe reaction was quenched with MeOH
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-b1533df2608d48dba637459b9cf06198
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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