Methanol → 2-(3-{5-[5-(1-Amino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-2-hydroxymethyl-phenyl)-6-tert butyl-8-fluoro-2H-phthalazin-1-one

HRID 2069866Notes

Reaction equation

HRID 2069866 reaction equation
[NH2:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=[C:14]([C:20]3[CH:30]=[CH:29][CH:28]=[C:27]([N:31]4[N:40]=[CH:39][C:38]5[C:33](=[C:34]([F:45])[CH:35]=[C:36]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:37]=5)[C:32]4=[O:46])[C:21]=3[CH2:22][O:23]C(=O)C)[CH:13]=2)=[N:9][CH:10]=1)([CH3:4])[CH3:3].O.[OH-].[Li+].CO>O1CCOCC1>[NH2:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=[C:14]([C:20]3[C:21]([CH2:22][OH:23])=[C:27]([N:31]4[N:40]=[CH:39][C:38]5[C:33](=[C:34]([F:45])[CH:35]=[C:36]([C:41]([CH3:42])([CH3:43])[CH3:44])[CH:37]=5)[C:32]4=[O:46])[CH:28]=[CH:29][CH:30]=3)[CH:13]=2)=[N:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 59473787Acetic acid 2-{5-[5-(1-amino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzyl ester

Product 1

HCID 469089972-(3-{5-[5-(1-Amino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-2-hydroxymethyl-phenyl)-6-tert butyl-8-fluoro-2H-phthalazin-1-oneYield 679.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Acetic acid 2-{5-[5-(1-amino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzyl ester (159 mg, 0.0255 mmol) was dissolved in dioxane (3 ml). 2 M lithium hydroxide monohydrate solution (0.76 ml, 1.53 mmol) was added and stirred for 3hr at r.t. MeOH was added and the mixture purified purified by chromatography. Isolated product was dried under high vacuum at 50° C. to give 2-(3-{5-[5-(1-Amino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-2-hydroxymethyl-phenyl)-6-tert butyl-8-fluoro-2H-phthalazin-1-one (101 mg, 68%) as a off-white crystalline product. MS (H+)=583.3.

Workup

  1. customthe mixture purified
  2. custompurified by chromatography
  3. customIsolated product was dried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-130e8ef3cfee4beba235b83ffb462320
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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