Triethylamine → HCID 178448505, compound

HRID 254617Notes

Reaction equation

HRID 254617 reaction equation
I.[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]1=[NH:13])[CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:31][CH3:32])=[C:26]([CH:30]=1)[C:27](Cl)=[O:28]>C(Cl)Cl>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[N:13]\[C:27](=[O:28])[C:26]1[CH:30]=[C:22]([Cl:21])[CH:23]=[CH:24][C:25]=1[O:31][CH3:32])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 66851866HCID 66851866, compound

Product 1

HCID 178448505HCID 178448505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1A (312 mg, 1 mmol) and triethylamine (0.42 mL, 3 mmol) in CH2Cl2 (15 mL) at 0° C. was added 5-chloro-2-methoxybenzoyl chloride (Waterstone, 205 mg, 1 mmol), the mixture was allowed to warm to room temperature and was stirred for 14 hours. The solution was washed sequentially with water, brine, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ: 0.93 (t, J=7 Hz, 3H), 1.35 (sextet, J=7 Hz, 2H), 1.68 (quintet, J=7 Hz, 2H), 2.21 (s, 3H), 2.26 (s, 3H), 3.78 (s, 3H), 4.26 (t, J=7 Hz, 2H), 7.10 (d, J=9 Hz, 1H), 7.44 (d-d, J=9 Hz, 3 Hz, 1H), 7.70 (d, J=3 Hz, 1H); MS (ESI+) m/z 353 (M+H)+.

Workup

  1. washThe solution 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 column chromatography

Sources & evidence

ORD record
ord-280014c58fe3453dadf033f424fd0e23
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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