Tetrahydrofuran → 6-[3-(2-ethoxy-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 1028211Notes

Reaction equation

HRID 1028211 reaction equation
O1CCCC1.[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]2.[CH2:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35])[CH3:25]>C(OCC)(=O)C.C(Cl)Cl>[C:20]([O:19][C:17]([N:12]1[CH2:11][CH2:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([NH:6][C:34]([NH:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH2:24][CH3:25])=[O:35])[CH:8]=2)[CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 79374Benzene, 1-ethoxy-2-isocyanato-HCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 669360506-[3-(2-ethoxy-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A tetrahydrofuran (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (981 mg) and 2-ethoxyphenyl isocyanate (0.9 mL) was stirred at room temperature for 4 hours and then concentrated. The residue was purified by chromatography (hexane:ethyl acetate=5:1→1:1 and then methylene chloride:ethyl acetate=1:0→1:1) to obtain the title compound (1.62 g, quantitative yield) as a pale yellow solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (hexane

Sources & evidence

ORD record
ord-47a226b231fd40ceaf061e5611d3db4d
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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