Tetrahydrofuran → HCID 89980374, compound

HRID 532914Notes

Reaction equation

HRID 532914 reaction equation
[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][N:16]=[C:15]([C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)[CH:14]=[C:9]12)[CH3:3].[BH4-].[Na+].[CH2:28]1COCC1>CCOC(C)=O.CCOCC>[CH3:28][O:1][CH:2]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][N:16]=[C:15]([C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)[CH:14]=[C:9]12)[CH3:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 89979547HCID 89979547, compound

Product 1

HCID 89980374HCID 89980374, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

9-(1-hydroxyethyl)-2-(1-methyl-1H-pyrazol-3-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one. 47-2. A solution of 47-1 (400 mg, 1.20 mmol) in THF (30 mL) was treated with NaBH4 (23 mg, 0.60 mmol) and the mixture was stirred at RT for 48 h. The mixture was then diluted with AcOEt, and washed with H2O. The org. phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained was purified by flash chroatography (SiO2, DCM to DCM/MeOH 95:5) to afford a yellow oil that was suspended in Et2O. The suspension was filtered and the filter cake was dried on vacuo to give the title compound (145 mg) as a light yellow solid. UPLC-MS: MS 337.3 (M+H+); UPLC rt 0.60 min. 1H NMR (400 MHz, CHLOROFORM-d): δ ppm 1.49 (d, J=6.26 Hz, 3 H); 1.82-1.96 (m, 1 H); 2.86-3.09 (m, 2 H); 3.75-3.99 (m, 2 H); 3.92 (s, 3 H); 4.48 (d, J=12.12 Hz, 2 H); 5.17 (d, J=3.52 Hz, 1 H); 6.82 (br. s., 1 H); 7.19 (s, 1 H); 7.32-7.40 (m, 2 H); 7.61 (d, J=7.82 Hz, 1 H); 7.64 (d, J=7.82 Hz, 1 H).

Workup

  1. washwashed with H2O
  2. dry with materialphase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customwas purified by flash chroatography (SiO2, DCM to DCM/MeOH 95:5)
  7. customto afford a yellow oil that
  8. filtrationThe suspension was filtered
  9. customthe filter cake was dried on vacuo

Sources & evidence

ORD record
ord-e8c4f9592e39447a919fca97e0b23234
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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