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Water → 6-Tert-butyl-2-[4-[5-[(1-ethylpyrazol-3-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-8-fluoro-phthalazin-1-one

HRID 1185173
Notes
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Reaction equation

HRID 1185173 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([N:28]2[N:37]=[CH:36][C:35]3[C:30](=[C:31]([F:42])[CH:32]=[C:33]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:34]=3)[C:29]2=[O:43])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH:18][C:19]2[CH:23]=[CH:22][N:21]([CH2:24][CH3:25])[N:20]=2)[C:15](=[O:26])[N:14]([CH3:27])[CH:13]=1)(=O)C.C1COCC1.O>ClCCl>[C:38]([C:33]1[CH:34]=[C:35]2[C:30](=[C:31]([F:42])[CH:32]=1)[C:29](=[O:43])[N:28]([C:7]1[C:6]([CH2:5][OH:4])=[C:11]([C:12]3[CH:17]=[C:16]([NH:18][C:19]4[CH:23]=[CH:22][N:21]([CH2:24][CH3:25])[N:20]=4)[C:15](=[O:26])[N:14]([CH3:27])[CH:13]=3)[CH:10]=[CH:9][N:8]=1)[N:37]=[CH:36]2)([CH3:40])([CH3:39])[CH3:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 86684027(2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(5-(1-ethyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)pyridin-3-yl)methyl acetate

Product 1

HCID 866840286-Tert-butyl-2-[4-[5-[(1-ethylpyrazol-3-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-8-fluoro-phthalazin-1-oneYield 19%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

Into a 1 dram vial was added 142d (1 equiv) in a 4:1 mixture of THF and water (1 mL) Lithium hydroxide (1.5 equiv) was then added to the mixture and the reaction was stirred at room temperature for 16 hours. The reaction was then diluted with dichloromethane (3 mL) and washed with water (2×3 mL). The organic layer was collected, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by reverse-phase chromatography to give 142 (7.6 mg, 19% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.52 (d, J=2.5 Hz, 1H), 8.16 (s, 1H), 8.06 (d, J=2.5 Hz, 1H), 7.89 (m, 1H), 7.75 (dd, J=13.1, 1.9 Hz, 1H), 7.53 (d, J=2.2 Hz, 1H), 7.51 (d, J=12.6 Hz, 1H), 7.40 (d, J=2.1 Hz, 1H), 6.07 (s, 1H), 4.46 (br s 1H), 4.00 (q, J=7.2 Hz, 2H), 3.60 (s, 3H), 3.17 (s, 2H), 1.39 (s, 9H), 1.34 (t, J=7.2 Hz, 3H). ES-MS m/z 544.3 [M+1].

Workup

  1. additionwas then added to the mixture
  2. washwashed with water (2×3 mL)
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-c445a78533d84cc8a7d7bb6d0daf5493
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669251B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes