Potassium Carbonate → 6-tert-Butyl-8-fluoro-2-(2-hydroxymethyl-3-{6-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-pyridazin-4-yl}-phenyl)-2H-phthalazin-1-one

HRID 402936Notes

Reaction equation

HRID 402936 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[C:32]([NH:34][C:35]4[CH:40]=[CH:39][C:38]([C:41]([N:43]5[CH2:48][CH2:47][O:46][CH2:45][CH2:44]5)=[O:42])=[CH:37][N:36]=4)[N:31]=[N:30][CH:29]=3)[C:18]=1[CH2:19][O:20]C(=O)C)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[C:32]([NH:34][C:35]4[CH:40]=[CH:39][C:38]([C:41]([N:43]5[CH2:48][CH2:47][O:46][CH2:45][CH2:44]5)=[O:42])=[CH:37][N:36]=4)[N:31]=[N:30][CH:29]=3)[C:18]=1[CH2:19][OH:20])[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86686833acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{6-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-pyridazin-4-yl}-benzyl ester

Product 1

HCID 866868356-tert-Butyl-8-fluoro-2-(2-hydroxymethyl-3-{6-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-pyridazin-4-yl}-phenyl)-2H-phthalazin-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{6-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-pyridazin-4-yl}-benzyl ester (240 mg, 0.37 mmol) was dissolved in methanol (10 ml). K2CO3 (102 mg, 0.74 mmol) was added at room temperature and the mixture was stirred at that temperature for 2 hours. After the completion of the reaction, the mixture was filtered. The filtrate was washed with water, dried over sodium sulfate and concentrated. The desired product was obtained as a yellow solid (150 mg, yield 67%). 1H NMR (300 MHz, DMSO): δ 10.56 (s, 1H), 8.96 (d, J=1.9 Hz, 1H), 8.55-8.51 (m, 1H), 8.34 (d, J=2.2 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.85-7.73 (m, 3H), 7.65-7.47 (m, 3H), 4.88-4.80 (m, 1H), 4.28 (ddd, J=4.3, 3.1, 2.0 Hz, 2H), 3.65-3.46 (m, 8H), 1.38 (s, 9H). LC-MS: 610[M+1]+, tR=1.389 min. HPLC: 97.93% at 214 nm, 98.77% at 254 nm, tR=3.532 min.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe mixture was filtered
  3. washThe filtrate was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-10d9eed72b314a3d8d037390c9b6ecec
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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