1,2-Dichloroethane → HCID 136352248, compound

HRID 1047533Notes

Reaction equation

HRID 1047533 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[NH:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([NH2:48])[CH:46]=2)[N:41]([CH:49]2[CH2:54][CH2:53][CH2:52][CH2:51][O:50]2)[N:40]=1>CN(C=O)C>[NH:32]1[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[N:30]=[C:31]1[C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([NH:48][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[CH:46]=2)[N:41]([CH:49]2[CH2:54][CH2:53][CH2:52][CH2:51][O:50]2)[N:40]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 99683-Fluorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

Product 1

HCID 136352248HCID 136352248, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluorobenzoic acid (10 mg, 0.029 mmol), HOBt (6 mg, 0.044 mmol), EDC (9 mg, 0.045 mmol) and sodium bicarbonate (2.5 mg, 0.029 mmol) were added to a solution of 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (10 mg, 0.029 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 chromatography (6% CH3OH/CH2Cl2) afforded the title compound (8 mg) as a off white solid. 1H NMR (400 MHz, CDCl3): δ 8.40 (d, 1H, J=1.6 Hz), 8.15-8.13 (m, 2H), 7.95 (s, 1H), 7.58 (m, 2H), 7.52 (d, 1H, J=9.6 Hz), 7.42-7.36 (m, 2H), 7.21 (m, 2H), 5.69 (dd, 1H, J=2.4 and 9.2 Hz), 3.99 (m, 1H), 3.72 (m, 1H), 2.55 (m, 1H), 2.06 (m, 2H), 1.67 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-dc7df14d8ab646b1a7f77563ddcc8e35
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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