Water → HCID 67545805, compound

HRID 717232Notes

Reaction equation

HRID 717232 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH2:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:27][CH3:28])=[C:22]([CH:26]=1)[C:23](Cl)=[O:24].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:23](=[O:24])[C:22]2[CH:26]=[C:18]([Cl:17])[CH:19]=[CH:20][C:21]=2[O:27][CH3:28])[N:7]([CH2:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 67546777HCID 67546777, compound

Product 1

HCID 67545805HCID 67545805, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of the product from Example 12C (447 mg, 2.0 mmol) and the product from Step A of Example 11C (410 mg, 2.0 mmol) in CH2Cl2 (8 mL) at about 0° C. was added triethylamine (0.34 mL, 2.4 mmol) dropwise. After stirring for 1 hour at room temperature, water (10 mL) was added to quench the reaction, and CH2Cl2 (20 mL) was added. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography using an Analogix® IT280™ eluting with ethyl acetate/Hexanes in 0-50% gradient to yield the title compound (330 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.26 (s, 1H), 7.81 (d, J=2.71 Hz, 1H), 7.62 (dd, J=8.98, 2.88 Hz, 1H), 7.28 (d, J=9.15 Hz, 1H), 6.31 (s, 1H), 4.05-4.23 (m, 3H), 3.97 (s, 3H), 3.54-3.72 (m, 2H), 1.83-2.01 (m, 1H), 1.62-1.82 (m, 2H), 1.43-1.60 (m, 1H), 1.24 (s, 9H). MS (ESI) m/z 392 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction, and CH2Cl2 (20 mL)
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography
  10. washeluting with ethyl acetate/Hexanes in 0-50% gradient

Sources & evidence

ORD record
ord-83042df396d645758a4ac60de43b69f3
Source dataset
uspto-grants-2015_11
Patent number
US09193713B2

Reaction notes

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