Triethylamine → [2-Propyl-5-(1,1,3-trioxo-1,3-dihydro-1lambda6-benzo[d]isothiazol-2-yl)-benzoimidazol-1-yl]-acetic acid tert-butyl ester

HRID 15535Notes

Reaction equation

HRID 15535 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](=[O:33])(=[O:32])[NH:11][C:12]1[CH:31]=[CH:30][C:15]2[N:16]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:17]([CH2:19][CH2:20][CH3:21])=[N:18][C:14]=2[CH:13]=1.CCN(CC)CC>CO>[C:26]([O:25][C:23](=[O:24])[CH2:22][N:16]1[C:15]2[CH:30]=[CH:31][C:12]([N:11]3[C:3](=[O:2])[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[S:10]3(=[O:33])=[O:32])=[CH:13][C:14]=2[N:18]=[C:17]1[CH2:19][CH2:20][CH3:21])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 8471Triethylamine3×HCID 67203427HCID 67203427, compound

Product 1

HCID 67201540[2-Propyl-5-(1,1,3-trioxo-1,3-dihydro-1lambda6-benzo[d]isothiazol-2-yl)-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

The product of step b.) (33 mg, 0.069 mmol) was stirred in methanol (2 mL) with Et3N (10 μL, 0.069 mmol) at 65° C. for two hours without change. The reaction was concentrated to dryness and redissolved in toluene (2 mL). Et3N (10 μL, 0.069 mmol) was added to the solution and the reaction was heated to 110° C. overnight. Additional Et3N (35 μL, 0.242 mmol) was added and the reaction was heated overnight to complete reaction. The reaction was then concentrated to give the sub-title compound that was used in crude form without purification. MS: ESI (positive): 456 (M+H).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in toluene (2 mL)
  3. temperaturethe reaction was heated overnight
  4. customreaction
  5. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-f6128a8659ec446c9f3f2996b643353f
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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