p-Toluenesulfonic acid → 4,4-Dimethyl-7-{2-[(pyridazin-4-ylmethylene)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 969692Notes

Reaction equation

HRID 969692 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH2:28])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:30]1[CH:35]=[CH:34][C:33]([CH:36]=O)=[CH:32][N:31]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:28]=[CH:36][C:33]3[CH:34]=[CH:35][N:30]=[N:31][CH:32]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 13011721Pyridazine-4-carbaldehydeHCID 695107067-(2-amino-benzoylamino)-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 695103724,4-Dimethyl-7-{2-[(pyridazin-4-ylmethylene)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(2-amino-benzoylamino)-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (512 mg, 1.3 mmol), pyridazine-4-carbaldehyde (140 mg, 1.3 mmol) and p-toluenesulfonic acid (10 mg) was heated at reflux in toluene (5 mL) for 1 h. The mixture was cooled to RT and diluted with CH2Cl2. NaBH4 (50 mg, 1.3 mmol) was added to the mixture followed by MeOH (2 mL). The mixture was stirred for 1 h. The crude material was purified with flash chromatography (SiO2, 5% MeOH/CH2Cl2) to give a yellow solid. MS (ES+): 488.0 (M+H)+. Calc'd for C28H33N5O3: 487.59.

Workup

  1. temperaturewas heated
  2. customThe crude material was purified with flash chromatography (SiO2, 5% MeOH/CH2Cl2)
  3. customto give a yellow solid

Sources & evidence

ORD record
ord-fd1c78ab5bf640a88e3ac7b6dd52b07c
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

Loading…