7-Methoxy-2-tetralone → HCID 22256423, compound

HRID 1866050Notes

Reaction equation

HRID 1866050 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[N+](C1C=CC=CC=1S([N:26]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=1)(=O)=O)([O-])=O.[BH3-]C#N.[Na+]>CO.C(OC)(OC)OC.C(O)(=O)C>[N:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][NH:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][NH:35][CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 777857-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydrideHCID 22708748N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-1,4-benzenedimethanamine

Product 1

HCID 22256423HCID 22256423, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

Using General Procedure G: 7-methoxy-2-tetralone (60 mg, 0.34 mmol), N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-1,4-benzenedimethanamine (100 mg, 0.24 mmol) and NaBH3CN (59 mg, 0.94 mmol) in MeOH (3 mL), trimethyl orthoformate (1.7 mL) and acetic acid (3 drops) were reacted for 3.5 hours. Following work-up, the crude material was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1) to give the desired product (71 mg, 52%) as a yellow foam.

Workup

  1. customthe crude material was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 98:1:1)

Sources & evidence

ORD record
ord-c0b86eb84e804eeca6e7295226b17143
Source dataset
uspto-grants-2009_12
Patent number
US07629337B2

Reaction notes

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