1,2-Dichloroethane → HCID 11597881, compound

HRID 1442685Notes

Reaction equation

HRID 1442685 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[O:18][C:19]3[CH:25]=[C:24]([C:26]([OH:28])=O)[CH:23]=[CH:22][C:20]=3[N:21]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].C(Cl)CCl.Cl.[CH3:38][NH:39][CH3:40]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:38][N:39]([CH3:40])[C:26]([C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:30])[C:2]([CH3:32])([CH3:31])[CH3:1])=[C:7]([CH3:29])[CH:8]=3)([CH2:15][CH3:16])[CH2:13][CH3:14])[O:18][C:19]=2[CH:25]=1)=[O:28]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 11568313HCID 11568313, compound

Product 1

HCID 11597881HCID 11597881, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzooxazole-6-carboxylic acid (150 mg, 0.343 mmol) in CH2Cl2 (5.0 mL) is treated with DMAP (125 mg, 1.03 mmol) and EDC (99 mg, 0.514 mmol). The mixture is stirred for 15 m at RT, and dimethylamine hydrochloride (42 mg, 0.514 mmol) is added. The reaction is stirred for 18 h and quenched with aqueous NH4Cl (5.0 mL). The organic layer is loaded onto a silica gel column and purified with 50% EtOAc/Hex to afford the title compound (125 mg, 79%). MS (ES) m/e: 465.3 (M+1).

Workup

  1. stirringThe reaction is stirred for 18 h
  2. customquenched with aqueous NH4Cl (5.0 mL)
  3. custompurified with 50% EtOAc/Hex

Sources & evidence

ORD record
ord-d89c77270b5b4baca1eac754b1070ac8
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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