Sodium borohydride → HCID 58574745, compound

HRID 1619412Notes

Reaction equation

HRID 1619412 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:25])[N:15]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:16]4=[N:17]3)=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(Cl)(Cl)Cl.CO>[OH:9][CH:8]([C:10]1[CH:19]=[C:18]2[C:13]([C:14](=[O:25])[N:15]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:16]3=[N:17]2)=[CH:12][CH:11]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58574122HCID 58574122, compound

Product 1

HCID 58574745HCID 58574745, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 3-(2-phenylacetyl)-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one, obtained from Example 21.3 (100 mg, 0.3 mmol) and excess NaBH4 in CHCl3/MeOH (10 mL, 1:1) was stirred at room temperature for 2 h. After quenching with water, the reaction solution was extracted with ethyl acetate (3×20 mL). The combined organic layers were concentrated. The residue was purified by silica gel chromatography to give the desired product. MS (ESI): 335 (MH+); 1H NMR (300 MHz, CDCl3) δ: 8.18-8.16 (d, J=8.19 Hz, 1H), 7.82 (s, 1H), 7.41-7.28 (m, 6H), 5.05-5.01 (t, J=7.65 Hz, 1H), 4.49-4.46 (t, J=5.01 Hz, 2H), 3.76 (brs, 1H), 3.36-3.33 (t, J=4.08 Hz, 2H), 3.23-3.20 (m, 2H), 2.00-1.86 (m, 6H).

Workup

  1. customAfter quenching with water
  2. extractionthe reaction solution was extracted with ethyl acetate (3×20 mL)
  3. concentrationThe combined organic layers were concentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-681b28e0d84940a493ea3015b6c3e3ab
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…