1,2-Dichloroethane → HCID 59625727, compound

HRID 2365617Notes

Reaction equation

HRID 2365617 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:2]1.[C:18]([O:22][C:23]([N:25]1[CH2:34][CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:35](O)=[O:36])[CH:31]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(Cl)CCl.CCN(CC)CC>C(Cl)Cl>[C:18]([O:22][C:23]([N:25]1[CH2:34][CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:35]([N:1]3[CH2:2][CH:3]([N:5]4[CH2:6][CH2:7][N:8]([C:11]([C:13]5[S:14][CH:15]=[CH:16][N:17]=5)=[O:12])[CH2:9][CH2:10]4)[CH2:4]3)=[O:36])[CH:31]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 113578872-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acidHCID 59625677(4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone

Product 1

HCID 59625727HCID 59625727, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 5e (651 mg, 2 mmol), 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester 17b (555 mg, 2 mmol), and EDC (466 mg, 3 mmol) in CH2Cl2 (20 mL) was added Et3N (0.84 mL, 6 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was extracted with CH2Cl2, and H2O after acidifying the water layer to pH-6 with 1N aqueous HCl. The organic solution was dried over Na2SO4 and concentrated. Purification of the residue by flash column chromatography (silica gel, 2% MeOH/EtOAc) gave 17c (826 mg). MS m/z (M+H+) 512.1.

Workup

  1. extractionThe mixture was extracted with CH2Cl2, and H2O
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification of the residue by flash column chromatography (silica gel, 2% MeOH/EtOAc)

Sources & evidence

ORD record
ord-04eef8aeecab43478e6478c524ec5f75
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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