Dimethylamine → HCID 136056836, compound

HRID 1467568Notes

Reaction equation

HRID 1467568 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[C:25]4=[N:26][NH:27][C:28](=[O:33])[C:29]5[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=54)[NH:22][CH:21]3[C:34]3[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=3)=[CH:16][CH:15]=2)=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:42][NH:43]C.[BH4-].[Na+]>CO>[C:1]([N:6]1[CH2:7][CH2:8][N:9]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]3[C:25]4=[N:26][NH:27][C:28](=[O:33])[C:29]5[CH:30]=[CH:31][CH:32]=[C:23]([C:24]=54)[NH:22][CH:21]3[C:34]3[CH:41]=[CH:40][C:37]([CH2:38][NH:43][CH3:42])=[CH:36][CH:35]=3)=[CH:18][CH:19]=2)=[O:13])[CH2:10][CH2:11]1)(=[O:5])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 4311764Sodium borohydrideHCID 136374687HCID 136374687, compound

Product 1

HCID 136056836HCID 136056836, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(9-(4-(4-isobutyrylpiperazine-1-carbonyl)phenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde (40 mg, 0.07 mmol) and 33% dimethylamine aq solution (17 mg, 0.14 mmol) in methanol (10 mL) was stirred at room temperature for 40 min. Then the mixture was cooled to 0° C. Sodium borohydride (4 mg, 0.11 mmol) was added. After the addition, the mixture was stirred at this temperature for 2 hr. Methanol was removed under reduced pressure. The residue was washed with ethyl acetate/methanol (10/1) and filtered. The filtrate was concentrated to give the crude product. The crude product was purified by prep-HPLC to give the compound 9-(4-(4-isobutyrylpiperazine-1-carbonyl)phenyl)-8-(4-((methylamino)methyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7 H)-one (18 mg, yield 49%) as a light yellow solid. 1H-NMR (400 MHz, CD3OD) δ (ppm): 1.10-1.12 (d, J=6.8 Hz, 6H), 2.67 (s, 3H), 2.81 (brs 1H), 3.33-3.70 (m, 8H), 4.12 (s, 2H), 4.43-4.75 (d, J=7.6 Hz, 1H), 4.88 (d, J=7.4 Hz, 1H), 7.22-7.27 (m, 3H), 7.31-7.37 (m, 4H), 7.42-7.44 (d, J=8.0 Hz, 2H), 7.56-7.58 (d, J=7.2 Hz, 1H), 7.64-7.68 (t, J=8.0 Hz, 1H); LC-MS (ESI) m/z: 579 (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. washThe residue was washed with ethyl acetate/methanol (10/1)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto give the crude product
  9. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-81c9a4c74eaf45a0a54dbade15c204b4
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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