Triethylamine → HCID 59316811, compound

HRID 2189806Notes

Reaction equation

HRID 2189806 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=O)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.O[NH:33][C:34](=[NH:54])[C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH:37]=[N:38][N:39]2[CH2:44][CH2:45][C:46]([CH3:53])([CH3:52])[C:47]([O:49][CH2:50][CH3:51])=[O:48]>CN(C=O)C.CCOC(C)=O.C(Cl)CCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:14][N:33]=[C:34]([C:35]3[CH:43]=[CH:42][CH:41]=[C:40]4[C:36]=3[CH:37]=[N:38][N:39]4[CH2:44][CH2:45][C:46]([CH3:52])([CH3:53])[C:47]([O:49][CH2:50][CH3:51])=[O:48])[N:54]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 180705825-Chloro-6-isopropoxynicotinic acidHCID 178471422HCID 178471422, compound

Product 1

HCID 59316811HCID 59316811, compoundYield 70.3%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (D31) (67.7 mg, 0.314 mmol) then triethylamine (88 μl, 0.628 mmol) followed by HOBT (57.7 mg, 0.377 mmol), EDC (72.3 mg, 0.377) and ethyl 4-{4-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}-2,2-dimethylbutanoate (D114) (100 mg, 0.314 mmol) were dissolved in DMF (4 ml) at room temperature then stirred at 50° C. for 5 days. The mixture was cooled to room temperature and diluted with EtOAc. The organic phase was washed with water, dried and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [15-40% EtOAc/cyclohexane] gave the title compound (110 mg, 67%) as a light yellow solid. MS (ES) C25H28ClN5O4 requires 497, found 498 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica gel [15-40% EtOAc/cyclohexane]

Sources & evidence

ORD record
ord-3818491086834178956362dea9dc7253
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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