1,2-Dichloroethane → HCID 67112542, compound

HRID 2284316Notes

Reaction equation

HRID 2284316 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[CH:20]4)=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[NH:27]1[C:35]2[C:30](=[CH:31][C:32](C(O)=O)=[CH:33][CH:34]=2)C=N1.[OH:39][C:40]1[C:48]2N=NN[C:44]=2[CH:43]=CC=1.C(N(CC)CC)C.NC1C=CC(N2CCC(O)CC2)=CC=1.C(Cl)CCl>CN(C=O)C>[CH:48]1([C:40]([NH:27][C:35]2[CH:30]=[CH:31][C:32]([N:22]3[C:23]4[C:19](=[CH:18][C:17]([C:15]([NH:14][C:11]5[CH:10]=[CH:9][C:8]([N:5]6[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]6)=[CH:13][CH:12]=5)=[O:16])=[CH:25][CH:24]=4)[CH:20]=[N:21]3)=[CH:33][CH:34]=2)=[O:39])[CH2:43][CH2:44]1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 167921071-(4-Aminophenyl)piperidin-4-olHCID 448287321H-Indazole-5-carboxylic acid--hydrogen chloride (1/1)HCID 67113319HCID 67113319, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67112542HCID 67112542, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 945 was prepared according to the general procedure described in Scheme IV. Preparation of N-(4-(4-hydroxypiperidin-1-yl)phenyl)-1H-indazole-5-carboxamide: 1H-indazole-5-carboxylic acid hydrochloride (100 mg, 0.50 mmol), hydroxybenzotriazole (7 mg, 0.05 mmol), triethylamine (0.2 mL, 1.3 mmol), and 1-(4-aminophenyl)piperidin-4-ol (193 mg, 1.00 mmol) were taken up in DMF (2.51 mL) and stirred. EDC (106 mg, 0.05 mmol) was added to the solution last. After the addition, the solution was stirred at room temperature for 24 h. The solution was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. Filtration and concentration gave the crude amide. Purification via flash chromatography 0-10% MeOH/CH2Cl2 gave 55 mg (32%) of the product as a white solid.

Workup

  1. additionAfter the addition
  2. stirringthe solution was stirred at room temperature for 24 h
  3. customThe solution was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and concentration
  8. customgave the crude amide

Sources & evidence

ORD record
ord-709179592d164c5b9647bae2f3e16733
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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