1,2-Dichloroethane → HCID 178521726, compound

HRID 1047567Notes

Reaction equation

HRID 1047567 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:31]=[CH:30][C:10]3[NH:11][C:12]([C:14]4[C:22]5[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=5)[N:16]([CH:24]5[CH2:29][CH2:28][CH2:27][CH2:26][O:25]5)[N:15]=4)=[N:13][C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.N1(O)C2C=CC=CC=2N=N1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[CH:51]1([C:54](O)=[O:55])[CH2:53][CH2:52]1>CN(C=O)C>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:31]=[CH:30][C:10]3[NH:11][C:12]([C:14]4[C:22]5[C:17](=[CH:18][CH:19]=[C:20]([NH:23][C:54]([CH:51]6[CH2:53][CH2:52]6)=[O:55])[CH:21]=5)[N:16]([CH:24]5[CH2:29][CH2:28][CH2:27][CH2:26][O:25]5)[N:15]=4)=[N:13][C:9]=3[CH:8]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 178507237HCID 178507237, compound

Product 1

HCID 178521726HCID 178521726, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(5-Morpholino-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (30 mg, 0.072 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (14.53 mg, 0.108 mmol), EDC (20.61 mg, 0.108 mmol) and sodium bicarbonate (6.02 mg, 0.072 mmol) was added to a solution of cyclopropanecarboxylic acid (6.17 mg, 0.072 mmol) in DMF (6 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash column chromatography (6% CH3OH/CH2Cl2) afforded the title compound (20 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.47 (d, 1H, J=1.6 Hz), 7.75 (dd, 1H, J=2.0 and 9.2 Hz), 7.67 (d, 1H, J=8.8 Hz), 7.55 (d, 1H, J=8.4 Hz), 7.14 (m, 1H), 7.05 (dd, 1H, J=2.0 and 8.4 Hz), 5.86 (dd, 1H, J=2.4 and 9.6 Hz), 3.98 (m, 1H), 3.87 (m 4H), 3.81 (m, 1H), 3.16 (m, 4H), 2.64 (m, 1H), 2.14 (m, 2H), 1.81 (m, 2H), 1.71 (m, 2H), 0.99 (m, 2H), 0.88 (m, 2H); ESI-MS [M+H]+:487.22.

Workup

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

Sources & evidence

ORD record
ord-68314b40ffb74a22a677d9f79660871e
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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