1,2-Dichloroethane → HCID 178453968, compound

HRID 1510932Notes

Reaction equation

HRID 1510932 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH2:27].C(Cl)CCl.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:18][C:19]([F:28])([F:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH:27][C:15]([C@@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:14][CH2:13]1)=[O:17]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 764472-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 178453971HCID 178453971, compound

Product 1

HCID 178453968HCID 178453968, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cis-4-({[(1,1-dimethylethyl) oxy]carbonyl}amino)cyclohexanecarboxylic acid (3.0 g, 12 mmol, 1.0 equiv) and 1-[2-(trifluoromethyl)phenyl]methanamine (1.9 mL, 14 mmol, 1.0 equiv) in CH2Cl2 (82 mL) at room temperature, DMAP (301 mg, 2.47 mmol, 0.2 equiv) was added. EDC (2.95 g, 15.4 mmol, 1.25 equiv), and diisopropylethylamine (DIEA, 2.7 ml, 15 mmol, 1.25 equiv) were added. Stirring was continued overnight at room temperature. The solution was diluted with CH2Cl2 (100 ml), washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL). The CH2Cl2 extracts were dried with MgSO4, filtered, and concentrated under reduced pressure to yield the title compound. MS (ES+): m/e 400.8 [M+Na]+.

Workup

  1. washwashed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL)
  2. dry with materialThe CH2Cl2 extracts were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6071ccf20c0f41d0a878c4e6cce5be4f
Source dataset
uspto-grants-2012_07
Patent number
US08212032B2

Reaction notes

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