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

HRID 351168Notes

Reaction equation

HRID 351168 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-59c746ad58034b13a7b0d9b241cb916e
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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