Water → HCID 67249963, compound

HRID 2175096Notes

Reaction equation

HRID 2175096 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]([C:19]3[CH:28]=[C:27]4[C:22]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][C:26]4=O)=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.[C:32]([BH3-])#[N:33].[Na+].O.[C:37](=O)([O-])O.[Na+]>CNC.C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:37][N:33]([CH3:32])[CH:26]1[C:27]2[CH:28]=[C:19]([C:17]3[N:18]=[C:13]([N:10]4[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[CH2:12][CH2:11]4)[CH:14]=[CH:15][CH:16]=3)[CH:20]=[CH:21][C:22]=2[C:23]([CH3:30])([CH3:31])[CH2:24][CH2:25]1

Participants

8

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 53251220HCID 53251220, compound

Product 1

HCID 67249963HCID 67249963, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 674DimethylamineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

50 mg (0.12 mmol) of 7-{6-[4-(5-hydroxypentyl)piperazin-1-yl]pyridin-2-yl}-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one are dissolved in 2 ml of 2M dimethylamine in THF, and 15 mg of sodium cyanoborohydride and 38 mg of titanium(IV) isopropoxide are added, and the mixture is stirred in a pressure vessel at 80° C. Water added to the reaction mixture, sodium hydrogencarbonate solution added, and the mixture extracted with ethyl acetate, dried and evaporated. The crude product is purified by means of prep HPLC.

Workup

  1. additionadded
  2. extractionthe mixture extracted with ethyl acetate
  3. customdried
  4. customevaporated
  5. customThe crude product is purified by means of prep HPLC

Sources & evidence

ORD record
ord-c46b97830d3e41e7abb5c50fee9c529b
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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