Methanol → HCID 131735189, compound

HRID 624261Notes

Reaction equation

HRID 624261 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][CH:14]4[CH2:15][CH2:16][O:17][C:5]34[C:4]=2[CH:3]=1.[H-].[Na+].[C:20]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CO>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:31][CH2:30][CH2:29][CH2:28][NH:27][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:7](=[O:12])[CH:6]3[CH2:13][CH:14]4[CH2:15][CH2:16][O:17][C:5]34[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 10868765tert-butyl N-(4-bromobutyl)carbamateHCID 68749629HCID 68749629, compound

Product 1

HCID 131735189HCID 131735189, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-chloro-3,3a,4,4a-tetrahydro-2H-furo[2′,3′:2,3]cyclobuta[1,2-c]quinolin-5(6H)-one (200 mg, 0.801 mmol) in dimethylformamide (4 ml) at 0° C. was slowly added sodium hydride (19 mg, 0.801 mmol) over 15 minutes. The suspension was allowed to warm to room temperature. The mixture stirred for 45 minutes and 4-(Boc-amino)butyl bromide (202 mg, 0.801 mmol) was added. The solution was stirred for 15 hours, followed by addition of 0.25 mL methanol. Column chromatography provided the title compound.

Workup

  1. customat 0° C.
  2. customover 15 minutes
  3. stirringThe solution was stirred for 15 hours

Sources & evidence

ORD record
ord-b7d5f61da550454b882ded1adf570d29
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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