1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178426696, compound

HRID 1443386Notes

Reaction equation

HRID 1443386 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][NH:13]3)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O:26][C:27]([NH:29][CH:30]([CH2:34][C:35]1[C:40]([CH3:41])=[CH:39][C:38]([C:42](=[O:44])[NH2:43])=[CH:37][C:36]=1[CH3:45])[C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].O.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:22]([O:26][C:27](=[O:28])[NH:29][CH:30]([CH2:34][C:35]1[C:36]([CH3:45])=[CH:37][C:38]([C:42](=[O:44])[NH2:43])=[CH:39][C:40]=1[CH3:41])[C:31](=[O:32])[N:13]1[CH:12]([C:9]2[NH:10][CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221476672-((Tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoic acidHCID 178420112HCID 178420112, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 178426696HCID 178426696, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 220 mg (0.8 mmol) of 3-(4-phenyl-1H-imidazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline, 269 mg (0.8 mmol) of 2-tert-butoxycarbonylamino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid, 216 mg (1.6 mmol) of of hydroxybenzotriazole hydrate and 184 mg (0.96 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added 3 mL of dimethylformamide. The resulting mixture was allowed to stir overnight at room temperature under argon. The mixture was then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and concentrated. The product {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester was taken to the next step without further purification.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester was taken to the next step without further purification

Sources & evidence

ORD record
ord-6a68002c39a04f2391383683a9cc5bbc
Source dataset
uspto-grants-2010_02
Patent number
US07659402B2

Reaction notes

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