1,2-Dichloroethane → 2-(t-Butyloxycarbonyl)-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide

HRID 1584268Notes

Reaction equation

HRID 1584268 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([OH:20])=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([C:23]1[CH:37]=[CH:36][C:26]([CH2:27][N:28]2[C:32]([CH2:33][CH2:34][NH2:35])=[CH:31][N:30]=[CH:29]2)=[CH:25][CH:24]=1)#[N:22].ON1C2C=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[C:21]([C:23]1[CH:37]=[CH:36][C:26]([CH2:27][N:28]2[C:32]([CH2:33][CH2:34][NH:35][C:18]([C@@H:17]3[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][N:8]3[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[O:20])=[CH:31][N:30]=[CH:29]2)=[CH:25][CH:24]=1)#[N:22]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 158510473-(4-Cyanobenzyl) histamine

Product 1

HCID 701032202-(t-Butyloxycarbonyl)-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(t-butyloxycarbonyl)-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid (0.15 g, 0.54 mmol) and 3-(4-cyanobenzyl) histamine (0.122 g, 0.54 mmol) in DMF (5 mL) was added 1-hydroxybenzotriazole (0.083 g, 0.54 mmol), EDC (0.104 g, 0.54 mmol), and N-methylmorpholine (0.24 mL, 2.16 mmol). After stirring for 18 hr. the mixture was evaporated in vacuo and the residue was partitioned with EtOAc (50 mL) and saturated NaHCO3 (30 mL). The organic layer was washed with saturated NaCl solution (30 mL) and dried (MgSO4). Filtration was done which gave the title compound.

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was partitioned with EtOAc (50 mL) and saturated NaHCO3 (30 mL)
  3. washThe organic layer was washed with saturated NaCl solution (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration

Sources & evidence

ORD record
ord-1390598413ab4267aa2f06fbc05b6cd4
Source dataset
uspto-grants-1999_08
Patent number
US05932590

Reaction notes

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