Methylamine → HCID 136385221, compound

HRID 907786Notes

Reaction equation

HRID 907786 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[NH:12][CH:13]([C:21]4[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=4)[CH:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:5]([C:6]=23)=[N:4][NH:3]1.[BH4-].[Na+].[CH3:31][NH2:32]>>[CH3:31][NH:32][CH2:25][C:24]1[CH:23]=[CH:22][C:21]([CH:13]2[NH:12][C:7]3[C:6]4[C:5](=[N:4][NH:3][C:2](=[O:1])[C:11]=4[CH:10]=[CH:9][CH:8]=3)[CH:14]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 136344752HCID 136344752, compound

Product 1

HCID 136385221HCID 136385221, compoundYield 19%

Procedure

To 4-(3-oxo-9-phenyl-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde (59 mg, 0.16 mmol) was added methanamine (20 ml) and the mixture was stirred at room temperature for 2 h. Then 30 mg of sodium borohydride was added and stirred for another 2 h. The resulting mixture was evaporated under reduced pressure and purified by prep-HPLC. 11.5 mg of 8-(4-((methylamino)methyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one was obtained (yield: 19%). 1H-NMR (400 MHz, CD3OD) δ: 2.66 (s, 3H), 4.33-4.35 (d, J=8 Hz, 1H), 4.83-4.85 (d, J=7.6 Hz, 1H), 7.10-7.12 (m, 2H), 7.15-7.22 (m, 4H), 7.34-7.42 (m, 4H), 7.55-7.57 (m, 1H), 7.63-7.67 (m, 1H). LC-MS (ESI) m/z: 383 (M+1)+.

Workup

  1. stirringstirred for another 2 h
  2. customThe resulting mixture was evaporated under reduced pressure
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-1c841c4001b74d1fa830770a803243d6
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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