Lithium Hydroxide → HCID 67451765, compound

HRID 869206Notes

Reaction equation

HRID 869206 reaction equation
[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH:13][C:14]3[N:19]=[N:18][C:17]([C:20]4[O:24][N:23]=[C:22]([C:25](OCC)=[O:26])[CH:21]=4)=[CH:16][CH:15]=3)[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Li+].[OH-].[NH4+].[Cl-].C[N:35](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.CO.CN(C=O)C>[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH:13][C:14]3[N:19]=[N:18][C:17]([C:20]4[O:24][N:23]=[C:22]([C:25]([NH2:35])=[O:26])[CH:21]=4)=[CH:16][CH:15]=3)[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67451767HCID 67451767, compound

Product 1

HCID 67451765HCID 67451765, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(6((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)isoxazole-3-carboxylate (200 mg, 0.40 mmol) in THF/MeOH mixture (12 mL, 5:1) was added LiOH (1M, 1.2 mL) at rt. The reaction mixture was stirred overnight and concentrated. To this crude mixture was added NH4Cl (60 mg, 1.2 mmol), HBTU (246 mg, 0.65 mmol), DIEA (132 uL, 0.8 mmol), and DMF (5.0 mL). The mixture was stirred at rt overnight, filtered, and purified by reverse phase chromatography to provide the title compound as a white solid (23.2 mg, 16%), LRMS (M+H+) m/z 369.2.

Workup

  1. concentrationconcentrated
  2. stirringThe mixture was stirred at rt overnight
  3. filtrationfiltered
  4. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-6d5f97ef2fc747ad87c73cd92f79df09
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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