1,2-Dichloroethane → HCID 11477152, compound

HRID 599704Notes

Reaction equation

HRID 599704 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[S:21][C:20]3[CH:22]=[CH:23][C:24]([C:26](O)=[O:27])=[CH:25][C:19]=3[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:47][NH:48][CH3:49]>C(Cl)Cl.CCN(CC)CC>[CH3:47][N:48]([CH3:49])[C:26]([C:24]1[CH:23]=[CH:22][C:20]2[S: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])=[CH:18][C:19]=2[CH:25]=1)=[O:27]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 11419616HCID 11419616, compound

Product 1

HCID 11477152HCID 11477152, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-5-carboxylic acid (210 mg, 0.464 mmol) in CH2Cl2 (5.0 mL) is treated with Et3N (1.0 mL), HOBT (94 mg, 0.70 mmol), and EDC (134 mg, 0.70 mmol). The mixture is stirred for 10 min at RT, and dimethylamine (1.0 mL, 2.0 M in THF) is added. The reaction mixture is stirred for 18 h, loaded onto a silica gel column, and eluted with 65% EtOAc/Hex to afford the title compound (90 mg, 41%).

Workup

  1. stirringThe reaction mixture is stirred for 18 h
  2. washeluted with 65% EtOAc/Hex

Sources & evidence

ORD record
ord-ac89a4f0802d40afb58080c8281d5aa1
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

Loading…