1,2-Dichloroethane → HCID 11477152, compound

HRID 730988Notes

Reaction equation

HRID 730988 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-8071824c0a134479a63e2f9e95962556
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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