Dimethylamine → HCID 136385284, compound

HRID 907817Notes

Reaction equation

HRID 907817 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[NH:12][CH:13]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:14]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[CH:18]=O)[C:5]([C:6]=23)=[N:4][NH:3]1.[CH3:29][NH:30][CH3:31].[BH4-].[Na+]>CO>[CH3:29][N:30]([CH2:18][C:17]1[CH:16]=[C:15]([CH:14]2[C:5]3=[N:4][NH:3][C:2](=[O:1])[C:11]4[CH:10]=[CH:9][CH:8]=[C:7]([C:6]=43)[NH:12][CH:13]2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:31]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 4311764Sodium borohydrideHCID 136344723HCID 136344723, compound

Product 1

HCID 136385284HCID 136385284, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(3-oxo-8-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)benzaldehyde (45 mg, 0.12 mmol) and 33% dimethylamine solution (50.2 mg, 0.366 mmol) in methanol (5 mL) was stirred at room temperature for 1 h. Then the mixture was cooled to 0° C., sodium borohydride (6.95 mg, 0.184 mmol) was added portionwise. After the addition, the mixture was stirred at this temperature for 2 hr. Methanol was removed under reduced pressure. The residue was purified by prep-HPLC to give 9-(3-((dimethylamino)methyl)phenyl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (21 mg, yield 44%) as a light yellow solid. 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.59 (s, 3H), 2.75 (s, 3H), 4.11-4.27 (q, 2H), 4.31-4.34 (d, J=10.4 Hz, 1H), 4.68-4.71 (d, J=10.4 Hz, 1H), 7.17-7.30 (m, 9H), 7.33-7.37 (t, J=7.6 Hz, 1H), 7.56-7.58 (d, J=7.6 Hz, 1H), 7.60-7.64 (t, J=8.0 Hz, 1H); LC-MS (ESI) m/z: 396(M+1)+.

Workup

  1. temperatureThen the mixture was cooled to 0° C.
  2. additionAfter the addition
  3. stirringthe mixture was stirred at this temperature for 2 hr
  4. customMethanol was removed under reduced pressure
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-2a6ff63b9f214eb8afa274f8249086a7
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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