Dimethylformamide → Morpholino 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)imidazo[1,5-a]quinoline-5-carboxamide

HRID 1955444Notes

Reaction equation

HRID 1955444 reaction equation
N1([C:6]2[C:7](O)=[N:8][C:9]3[C:14]([C:15]=2[C:16]([NH2:18])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=3)CCCC1.C[C:21](C)([O-:23])[CH3:22].[K+].[C:26]1([CH3:36])C=CC(S(Cl)(=O)=O)=CC=1.C[C:38]([C:41]1[O:45][N:44]=[C:43]([CH2:46][N+:47]#[C-:48])[N:42]=1)([CH3:40])[CH3:39].C[N:50](C=O)C>C1COCC1>[O:23]1[CH2:21][CH2:22][N:50]([C:48]2[N:8]3[C:9]4[C:14]([C:15]([C:16]([NH2:18])=[O:17])=[CH:6][C:7]3=[C:46]([C:43]3[N:42]=[C:41]([CH:38]5[CH2:39][CH2:40]5)[O:45][N:44]=3)[N:47]=2)=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH2:26][CH2:36]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 107257105-(1,1-Dimethylethyl)-3-isocyanomethyl-1,2,4-oxadiazoleHCID 23665647Potassium tert-butoxide2×HCID 178513705HCID 178513705, compound

Product 1

HCID 70067464Morpholino 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)imidazo[1,5-a]quinoline-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To morpholino 2-hydroxyquinoline-4-carboxamide (VI, Step I, 0.47 g) in THF (15 ml) and dry DMF (2 ml) cooled at -15° is added potassium tert-butoxide in THF (1M, 1.82 ml). The mixture is stirred for 15 min, after which p-toluenesulfonyl chloride (0.347 g) is added. After stirring for 40 min. 5-cyclopropyl-3-isocyanomethyl-1,2,4-oxadiazole (IX, 0.300 g) is added, followed by potassium tert-butoxide (1M, 2.00 ml). The mixture is stirred an for additional 2 hr, quenched with several drops of aqueous sodium bicarbonate, and taken to dryness under reduced pressure. The residue is chromatographed (silica gel; methanol/dichloromethane (2/98)) to give the product, which is crystallized from dichloromethane/ether/hexane to give the title compound, mp 250°-252°; MS (m/z) at 389; IR 1628, 1584, 1115. 1249 and 1274 cm-1.

Workup

  1. stirringAfter stirring for 40 min
  2. stirringThe mixture is stirred an for additional 2 hr
  3. customquenched with several drops of aqueous sodium bicarbonate
  4. customThe residue is chromatographed (silica gel; methanol/dichloromethane (2/98))
  5. customto give the product, which
  6. customis crystallized from dichloromethane/ether/hexane

Sources & evidence

ORD record
ord-36b1bc4fcced469192658bcde006db06
Source dataset
uspto-grants-1998_07
Patent number
USRE035840

Reaction notes

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