Water → HCID 57894427, compound

HRID 1822166Notes

Reaction equation

HRID 1822166 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH:14]([C:18]1[N:19]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([Cl:27])=[CH:22][CH:21]=2)[CH:15]([CH3:17])[CH3:16])[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN([CH2:40][CH3:41])CC.[C:42]1(C)[CH:47]=C[C:45]([C:48](Cl)=[O:49])=[CH:44][CH:43]=1.[OH2:52]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:28]([N:19]1[C:20]2[C:25](=[CH:24][C:23]([Cl:27])=[CH:22][CH:21]=2)[CH:26]=[C:18]1[CH:14]([N:5]([CH2:4][CH2:3][CH2:2][N:1]1[C:40](=[O:52])[C:41]2[C:45](=[CH:44][CH:43]=[CH:42][CH:47]=2)[C:48]1=[O:49])[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:15]([CH3:17])[CH3:16])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 11590985HCID 11590985, compound

Product 1

HCID 57894427HCID 57894427, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of product of step 9 (0.1 mmol) in 2 mL of anhydrous DCM at 0° C., was added DMAP (0.01 mmol), Et3N (0.4 mmol), and p-toluoyl chloride (0.4 mmol). The mixture was stirred at room temperature for 1 h. The solution was poured into water, and extracted with EtOAc (×3). The organic layers were combined, washed with H2O (×3), brine (×3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography (10% EtOAc:hexane) to yield 50 mg of title compound.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with H2O (×3), brine (×3)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe material was purified by flash chromatography (10% EtOAc:hexane)

Sources & evidence

ORD record
ord-8e41282759284e1b9e2d66a0c9c8687d
Source dataset
uspto-grants-2009_10
Patent number
US07608723B2

Reaction notes

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