1,2-Dichloroethane → HCID 57980110, compound

HRID 1677128Notes

Reaction equation

HRID 1677128 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[CH2:48][N:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1>ClCCl.CN(C=O)C.C(OCC)(=O)C.O>[N:49]1([CH2:48][C@@H:44]2[CH2:45][CH2:46][CH2:47][N:43]2[C:15]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=3)=[CH:14][CH:13]=2)=[O:17])[CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

10

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27827194'-(Trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 57980110HCID 57980110, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Procedure B′: 4′-Trifluoromethyl-biphenyl-4-carboxylic acid (2.7 g, 10.1 mmol) is suspended in dichloromethane (100 mL) and DMF (100 mL). EDC (2.33 g, 12.2 mmol) and HOBt (1.64 g, 12.2 mmol) were added at room temperature in that order. DIEA (4.4 mL, 25.3 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (1.56 g, 10.1 mmol) are added to the mixture. The mixture is stirred at room temperature for overnight. Water and ethyl acetate are added to the mixture. The aqueous layer is extracted with dichlormethane (2×), followed by ethyl acetate (2×). The combined organic layers are washed with brine (3×), dried over Na2SO4 and evaporated. The crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 10% 2M NH3 in MeOH/CH2Cl2) give the product. MS (ES+) 403.2

Workup

  1. extractionThe aqueous layer is extracted with dichlormethane (2×)
  2. washThe combined organic layers are washed with brine (3×)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 10% 2M NH3 in MeOH/CH2Cl2)
  6. customgive the product

Sources & evidence

ORD record
ord-592672992e7842938aae6d213320aa7c
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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