1,2-Dichloroethane → HCID 69120459, compound

HRID 899874

Reaction equation

HRID 899874 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:18][O:19][C:20]([C:22]1[CH:39]=[CH:38][CH:37]=[CH:36][C:23]=1[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([OH:35])=O)=[CH:28][CH:27]=1)=[O:21].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:33](=[O:35])[CH2:32][C:29]1[CH:28]=[CH:27][C:26]([O:25][CH2:24][C:23]2[CH:36]=[CH:37][CH:38]=[CH:39][C:22]=2[C:20]([O:19][CH3:18])=[O:21])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 60663854N-(2,4-difluorobenzyl)-N-heptylamineHCID 68869545[(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid

Product 1

HCID 69120459HCID 69120459, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(2,4-Difluorobenzyl)-N-heptylamine (106 mg, 0.44 mmol) was added into (4-{[2-(methoxycarbonyl)benzyl]oxy}phenyl)acetic acid (120 mg, 0.4 mmol) in DCM (10 ml) and followed by EDC (84.3 mg, 0.44 mmol) and then DMAP (54 mg, 0.44 mmol). The mixture was stirred at room temperature overnight, and then washed with 1% hydrochloric acid, water and brine and dried with magnesium sulphate and evaporated. Chromatography of the residue on a column (ISOLUTE®SI, 5 g/15 ml) using DCM and MeOH/DCM (0.5:99.5) as eluant gave 155 mg desired product, yield 74%.

Workup

  1. washwashed with 1% hydrochloric acid, water and brine
  2. dry with materialdried with magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-f9ffef3e696e4d47b5b9e68f6ac3ecaf
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Linked notes

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