Triethylamine → HCID 59656648, compound

HRID 2054918Notes

Reaction equation

HRID 2054918 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.[Si]([N:35]=[C:36]=[O:37])(C)(C)C>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[CH:12][C:11]([CH2:21][CH2:22][NH:23][C:36]([NH2:35])=[O:37])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 11450439HCID 11450439, compound

Product 1

HCID 59656648HCID 59656648, compoundYield 15%

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, 0.065 g, 0.18 mmol) and triethylamine (0.07 mL, 0.5 mmol) in DMF (1 mL) at 0° C. was added TMSNCO (1.35 mL, 10.0 mmol). The reaction was allowed to warm to room temperature and stirred for 24 h. It was slowly quenched with water (0.5 mL) and the precipitates were removed by filtration. The filtrate was concentrated and the residue was purified by preparatory thin layer chromatography to afford the title compound (0.010 g, 15%).

Workup

  1. customIt was slowly quenched with water (0.5 mL)
  2. customthe precipitates were removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by preparatory thin layer chromatography

Sources & evidence

ORD record
ord-860503e94f5f4dc2b4295e6ecd3f311e
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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