Methanol → HCID 19593000, compound

HRID 613527Notes

Reaction equation

HRID 613527 reaction equation
C([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[CH:11][CH:10]=[CH:9][C:8]=2[NH:19][C:20](=[O:29])[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28])(O)=O.C([N:32]([CH2:35]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C[OH:55].[O:56]1CCOC[CH2:57]1>>[Cl:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:28])[C:21]=1[C:20]([NH:19][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][C:4]([NH:32][C:35]([O:56][CH3:57])=[O:55])=[C:13]2[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[O:29]

Participants

6

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 199401P,P-Diphenylphosphinic azideHCID 19592805HCID 19592805, compound

Product 1

HCID 19593000HCID 19593000, compound

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-carboxy-8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)quinoline (147.6 mg) and triethylamine (12.2 mg) in dioxane was added diphenylphosphoryl azide (99.8 mg) at 90° C., and the mixture was stirred for 2 hours at the same temperature. After cooling to 70° C., methanol (12.2 mg) was added thereto and the mixture was stirred for 1 hour at 85° C. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (methanoldichloromethane) and crystallized from isopropyl alcohol to give 8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)-3-(methoxycarbonylamino)quinoline (21.3 mg).

Workup

  1. stirringthe mixture was stirred for 1 hour at 85° C
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (methanoldichloromethane)
  7. customcrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-ccb7a96eaafd4b93a88ec5aceb56f876
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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