1,2-Dichloroethane → N-(2-{[(3R)-1-(cis-2-Azidocyclohexyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

HRID 1809898Notes

Reaction equation

HRID 1809898 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[N:10]1[CH2:14][CH2:13][C@@H:12]([NH2:15])[CH2:11]1)=[N+:2]=[N-:3].[F:16][C:17]([F:32])([F:31])[C:18]1[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=1)[C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22].CCN(CC)CC.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCOC(C)=O>[N:1]([C@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[N:10]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[C:20]2[CH:28]=[CH:29][CH:30]=[C:18]([C:17]([F:16])([F:32])[F:31])[CH:19]=2)[CH2:11]1)=[N+:2]=[N-:3]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 86608974HCID 86608974, compound

Product 1

HCID 86608976N-(2-{[(3R)-1-(cis-2-Azidocyclohexyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamideYield 92.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (3R)-1-(cis-2-azidocyclohexyl)-pyrrolidin-3-amine (0.453 g, 1.842 mmol) and (3-trifluoromethyl-benzoylamino)-acetic acid (0.478 g, 1.934 mmol) in CH2Cl2 (15 mL) was added Et3N (0.57 mL, 4.06 mmol) followed by EDC (0.389 g, 2.03 mmol) and HOBt (0.287 g, 2.13 mmol). The mixture was stirred at room temperature for 3 h. Then the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3 and brine. The organic layer was dried (MgSO4), concentrated and flash chromatographed (EtOAc to 10% MeOH/EtOAc) to give 0.745 g of the title compound. MS (EI) calcd: (M+H)+=439.3. Found: 439.4.

Workup

  1. washwashed with saturated Na2CO3 and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed (EtOAc to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-c39929ca2e0d47afb6a61b3406dd8ce8
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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