Methanol → HCID 136404889, compound

HRID 907767Notes

Reaction equation

HRID 907767 reaction equation
O=[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[NH:12][CH:13](C4C=CC(C=O)=CC=4)[CH:14](C4C=CC(C=O)=CC=4)[C:5]([C:6]=23)=[N:4][NH:3]1.[BH4-].[Na+].[CH3:33][OH:34]>>[CH3:13][NH:12][CH2:7][C:6]1[CH:11]=[CH:10][C:2]([N:3]2[N:4]=[C:5]3[CH2:14][CH2:13][NH:12][C:7]4[C:6]3=[C:11]([CH:10]=[CH:9][CH:8]=4)[C:33]2=[O:34])=[CH:14][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 136374667HCID 136374667, compound

Product 1

HCID 136404889HCID 136404889, compoundYield 33%

Procedure

A mixture of 4,4′-(3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazine-8,9-diyl)dibenzaldehyde (80 mg, 0.21 mmol) and 27% methylamine alcohol solution (94 mg, 0.82 mmol) in methanol (10 mL) was stirred at room temperature for 40 min. The mixture was then cooled to 0° C. Sodium borohydride (24 mg, 0.64 mmol) was added. After the addition, the mixture was stirred at room temperature for 4 hr. Methanol was removed under reduced pressure. The residue was washed with ethyl acetate and filtered. The filtrate was concentrated to give 8,9-bis(4-((methylamino)methyl)phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (29.5 mg, yield 33%) as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 2.20 (d, J=8.8 Hz, 6H), 3.52-3.53 (d, J=2.4 Hz, 4H), 4.31-4.33 (d, J=6.4 Hz, 1H), 4.76-4.77 (d, J=6.4 Hz, 1H), 7.06-7.08 (d, J=6.4 Hz, 2H), 7.12-7.17 (m, 5H), 7.35-7.38 (t, J=6.4 Hz, 2H), 7.49-7.57 (t, J=10.0 Hz, 1H); LC-MS (ESI) m/z: 426(M+1)+.

Workup

  1. temperatureThe mixture was then cooled to 0° C
  2. additionAfter the addition
  3. stirringthe mixture was stirred at room temperature for 4 hr
  4. customMethanol was removed under reduced pressure
  5. washThe residue was washed with ethyl acetate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-05125327ac9f491193d4054dd91dc421
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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