Triethylamine → HCID 178448490, compound

HRID 254618

Reaction equation

HRID 254618 reaction equation
I.[CH2:2]([N:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:8][C:7]1=[NH:15])[CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([O:33][CH3:34])=[C:28]([CH:32]=1)[C:29](Cl)=[O:30]>C(Cl)Cl>[CH2:2]([N:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:8]/[C:7]/1=[N:15]\[C:29](=[O:30])[C:28]1[CH:32]=[C:24]([Cl:23])[CH:25]=[CH:26][C:27]=1[O:33][CH3:34])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 668521773-butyl-5-tert-butyl-1,3-thiazol-2(3H)-imine hydroiodide

Product 1

HCID 178448490HCID 178448490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 6A (1.4 g, ˜4 mmol) and triethylamine (1.4 mL, 10 mmol) in CH2Cl2 (35 mL) at 0° C. was added 5-chloro-2-methoxy-benzoyl chloride (820 mg, 4 mmol), the mixture was allowed to warm to room temperature was stirred for 14 hours. The mixture was washed sequentially with water, brine, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (6:2:2 Hexane-EtOAc-CH2Cl2) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ: 0.94 (t, J=7 Hz, 3H), 1.30 (m+s, 11H), 1.75 (m, 2H), 3.77 (s, 3H), 4.14 (t, J=7 Hz, 2H), 7.10 (d, J=9 Hz, 1H), 7.31 (s, 1H), 7.43 (d-d, J=9 Hz, 3 Hz, 1H), 7.65 (d, J=3 Hz, 1H); MS (ESI+) m/z 381 (M+H)+.

Workup

  1. washThe mixture was washed sequentially with water, brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography (6:2:2 Hexane-EtOAc-CH2Cl2)

Sources & evidence

ORD record
ord-ee0b6dfc72374d449795fd3ab4b79bfa
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Linked notes

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