Triethylamine → HCID 178454058, compound

HRID 2370738Notes

Reaction equation

HRID 2370738 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32][C:33]1[C:42]([OH:43])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH:35]=[CH:36][N:37]=[CH:38]2.[C:44]([O:48][C:49](=[O:58])[NH:50][C@H:51]1[CH2:56][CH2:55][C@H:54](O)[CH2:53][CH2:52]1)([CH3:47])([CH3:46])[CH3:45].C(N(CC)CC)C>ClCCl>[C:44]([O:48][C:49](=[O:58])[NH:50][C@H:51]1[CH2:52][CH2:53][C@@H:54]([O:43][C:42]2[C:33]([Br:32])=[C:34]3[C:39](=[CH:40][CH:41]=2)[CH:38]=[N:37][CH:36]=[CH:35]3)[CH2:55][CH2:56]1)([CH3:47])([CH3:45])[CH3:46]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1360928955-Bromo-6-isoquinolinolHCID 178418329HCID 178418329, compound

Product 1

HCID 178454058HCID 178454058, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.33 mL (5.75 g, 33 mmol) of diethyl azo dicarboxylate were added to 18 g (68.75 mmol) of triphenylphosphine in 500 mL of dichloromethane at 0° C. and stirred for 15 min. 6.16 g (27.5 mmol) 5-bromo-isoquinolin-6-ol (2), 5.92 g (27.5 mmol) (trans-4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester and 3.81 mL (33 mmol) triethyl amine were added. The mixture was stirred for 4 days. The precipitate was removed by filtration, washed with dichloromethane and the solvents were distilled off. The crude product was purified by flash chromatography using ethyl acetate/n-heptane as eluent to give 2.77 g (24%) of 85. Rt=1.37 min (Method #1). Detected mass: 421.1/423.1 (M+H+).

Workup

  1. stirringThe mixture was stirred for 4 days
  2. customThe precipitate was removed by filtration
  3. washwashed with dichloromethane
  4. distillationthe solvents were distilled off
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-3aab3c1c684343d38bf9afa73cc048c1
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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