Water → HCID 70662702, compound

HRID 1043002Notes

Reaction equation

HRID 1043002 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(N)=O.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][NH2:30].O.C(=O)([O-])O.[Na+].C(#[N:39])C>>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:30][CH2:29][C:25]4[S:24][CH:28]=[CH:27][CH:26]=4)=[C:3]([NH2:39])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 34005(2-Thienylmethyl)amineHCID 516892Sodium BicarbonateHCID 574655814-Chloro-7-(3,5-dimethylisoxazol-4-yl)-6-methoxyquinoline-3-carboxamide2×

Product 1

HCID 70662702HCID 70662702, compound

Conditions

Temperature
80 °C

Procedure

To a magnetically stirred solution 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see Intermediate 56, 1.5 g) in acetonitrile (10 ml) in a Shlenk tube was added (2-thienylmethyl)amine (1.53 g). The Shlenk tube was sealed and the reaction mixture heated at 80° C. for 24 h. The water was added to the reaction followed by an aqueous saturated solution of sodium hydrogen carbonate. The mixture was extracted with DCM and the organic phase dried over Na2SO4, filtered and concentrated to dryness. The resulting crude compound was purified by chromatography on silica gel (25 g) eluting with DCM/methanol (95:5) to give 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-N4-(2-thienylmethyl)-3,4-quinolinediamine (1.493 g) as a cream coloured powder. LC/MS: MH+409.12, [M−H]− 407.17, Rt 2.70 min

Workup

  1. customThe Shlenk tube was sealed
  2. extractionThe mixture was extracted with DCM
  3. dry with materialthe organic phase dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe resulting crude compound was purified by chromatography on silica gel (25 g)
  7. washeluting with DCM/methanol (95:5)

Sources & evidence

ORD record
ord-e3943fcaa9244b699bf8dcf6dc387212
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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