Tetrahydrofuran → HCID 89980374, compound

HRID 926287Notes

Reaction equation

HRID 926287 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 chromatography (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 chromatography (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-e2b567eaee8348c8a7ab5e25019f4a0c
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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