Triethylamine → HCID 11567018, compound

HRID 2242191Notes

Reaction equation

HRID 2242191 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][NH2:14])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])=O)(C)(C)C.C(N(CC)CC)C.[O:29]1[C:34]2[CH:35]=[CH:36][C:37]([C:39](Cl)=[O:40])=[CH:38][C:33]=2[O:32][CH2:31][CH2:30]1>ClCCl>[S:19]1[CH2:20][CH2:21][N:17]([C:15]([C@H:9]2[NH:8][CH2:12][C@@H:11]([CH2:13][NH:14][C:39]([C:37]3[CH:36]=[CH:35][C:34]4[O:29][CH2:30][CH2:31][O:32][C:33]=4[CH:38]=3)=[O:40])[CH2:10]2)=[O:16])[CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27761682,3-dihydro-1,4-benzodioxine-6-carbonyl chlorideHCID 69241294HCID 69241294, compound

Product 1

HCID 11567018HCID 11567018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 17D (31.6 mg, 0.1 mmol) in anhydrous dichloromethane (1 mL) was added triethylamine (0.021 mL, 0.15 mmol) followed by 2,3-dihydro-1,4-benzodioxine-6-carbonyl chloride (23.8 mg, 0.12 mmol). The mixture was shaken overnight at room temperature and concentrated under reduced pressure, MS (APCI) m/e 472 (M+H)+. The residue was dissolved in anhydrous dichloromethane (0.5 mL) and trifluoroacetic acid (0.5 mL) was added. The mixture was allowed to stir for 5 hours at room temperature, concentrated under reduced pressure, and the residue purified by reverse-phase HPLC to provide the titled compound. MS (ESI) m/e 372 (M+H)+; 1H NMR (500 MHz, CD3OD): δ ppm 1.75-2.4 (m, 1 H), 2.74 (m, 2 H), 3.15 (m, 3 H), 3.33 (m, 1 H), 3.47 (m, 3 H), 3.75 (m, 1 H), 3.87 (m, 1 H), 4.28 (m, 4 H), 4.51 (m, 1H), 4.66 (m, 2 H), 6.90 (dd, 1 H), 7.33 (m, 2 H).

Workup

  1. concentrationconcentrated under reduced pressure, MS (APCI) m/e 472 (M+H)+
  2. dissolutionThe residue was dissolved in anhydrous dichloromethane (0.5 mL)
  3. additiontrifluoroacetic acid (0.5 mL) was added
  4. stirringto stir for 5 hours at room temperature
  5. concentrationconcentrated under reduced pressure
  6. customthe residue purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-8a8a7e56e28a4b5d957ec65bfb43f74c
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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