Sodium borohydride → HCID 58574398, compound

HRID 1619311Notes

Reaction equation

HRID 1619311 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:25])[N:15]4[CH2:23][C:22](=[O:24])[CH2:21][CH2:20][C:16]4=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:25])[N:15]4[CH2:23][CH:22]([OH:24])[CH2:21][CH2:20][C:16]4=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58574175HCID 58574175, compound

Product 1

HCID 58574398HCID 58574398, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((3-fluorophenyl)ethynyl)-6H-pyrido[2,1-b]quinazoline-8,11(7H,9H)-dione (0.2 g, 0.6 mmol, 1 equiv) in THF (15 mL) was added NaBH4 (45.6 mg, 1.2 mmol, 2 equiv) in portions. After stirring at rt for 30 minute, the reaction mixture was quenched with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 335 (M+H+); 1H NMR (300 MHz, CDCl3) δ 8.24-8.21 (d, J=8.19 Hz, 1H), 7.76 (s, 1H), 7.56-7.53 (dd, J=8.22, 1.41 Hz, 1H), 7.37-7.34 (m, 2H), 7.27-7.26 (m, 1H), 7.13-7.06 (m, 1H), 4.53-4.51 (m, 1H), 4.34-4.28 (m, 1H), 4.05-3.99 (m, 1H), 3.52-3.22 (m, 1H), 3.03-2.93 (m, 1H), 2.23-2.16 (m, 1H), 2.11-2.02 (m, 2H). mGluR5 PAM EC50: +++. Fold shift at 10 μM: ++.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8ed442182ecf4869858043cb5ecfcb36
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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