Diisopropylethylamine → HCID 89768550, compound

HRID 1521806Notes

Reaction equation

HRID 1521806 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][NH2:13])[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[Cl:14][C:15]1[N:20]=[C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][C:29]([CH3:34])([C:31](O)=[O:32])[C:28](=[O:35])[NH:27][C:26]=3[CH:36]=2)[C:18]([F:37])=[CH:17][N:16]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C.C(OCC)(=O)C>[Cl:14][C:15]1[N:20]=[C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][C:29]([CH3:34])([C:31]([NH:13][CH2:12][CH2:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=4)=[O:32])[C:28](=[O:35])[NH:27][C:26]=3[CH:36]=2)[C:18]([F:37])=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 445579442-(3-Nitrophenyl)ethan-1-amine--hydrogen chloride (1/1)HCID 89768659HCID 89768659, compound

Product 1

HCID 89768550HCID 89768550, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-nitrophenyl)ethanamine hydrochloride (100.00 mg; 0.49 mmol; 1.00 eq.), 6-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid (SYN5052A) (174.06 mg; 0.49 mmol; 1.00 eq.), o-(7-azabenzotriazol-1-yl)-n,n,n′,n′-tetra-methyluronium hexafluorophosphate (375.28 mg; 0.99 mmol; 2.00 eq.) and N-ethyl-N-isopropylpropan-2-amine (0.32 ml; 1.97 mmol; 4.00 eq.) are placed into a scintillation vial equipped with a stir bar. The mixture is taken up in DMF (3.00 ml). The reaction mixture is stirred for 16 hours. Upon completion, the reaction mixture is diluted with ethyl acetate (100 mL) and extracted with brine solution. The organic layer is then dried over magnesium sulfate, filtered, concentrated and purified via Prep HPLC using a gradient of 10-50% acetonitrile in water with 0.1% trifluoroacetic acid modifier to give 6-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methyl-N-[2-(3-nitrophenyl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxamide (10) (226.4 mg; 0.45 mmol; 91.6%);

Workup

  1. customvial equipped with a stir bar
  2. extractionextracted with brine solution
  3. dry with materialThe organic layer is then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via Prep HPLC

Sources & evidence

ORD record
ord-7f8bd5288a214bc885a19f0e07b15882
Source dataset
uspto-grants-2015_07
Patent number
US09073944B2

Reaction notes

Loading…