1,2-Dichloroethane → HCID 136352257, compound

HRID 1047548Notes

Reaction equation

HRID 1047548 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[NH:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[C:36]1[C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[C:50]([NH2:53])[CH:51]=2)[N:46]([CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][O:55]2)[N:45]=1>CN(C=O)C>[NH:37]1[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[N:35]=[C:36]1[C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[C:50]([NH:53][C:13]([CH:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH2:12][CH2:11]3)=[O:15])[CH:51]=2)[N:46]([CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][O:55]2)[N:45]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acidHCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

Product 1

HCID 136352257HCID 136352257, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(Pyridin-4-yl)piperidine-4-carboxylic acid (14 mg, 0.068 mmol), HOBt (12 mg, 0.088 mmol), EDC (17 mg, 0.088 mmol) and sodium bicarbonate (5 mg, 0.059 mmol) were added to a solution of 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (20 mg, 0.059 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuum. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (12 mg).

Workup

  1. customthe solvent was removed in vacuum
  2. customPurification by flash chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-e4ad6138c6e147ed8c65ded0293f3037
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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