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1,2-Dichloroethane → 6-{3-[4-(Thiazole-2-carbonyl)-piperazin-1-yl]-azetidine-1-carbonyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 401644
Notes
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Reaction equation

HRID 401644 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 596257276-{3-[4-(Thiazole-2-carbonyl)-piperazin-1-yl]-azetidine-1-carbonyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
Yield 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-48e9d592934c415fb1a6e353e4595f19
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741887B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes