Pyridine → HCID 136352253, compound

HRID 1047541Notes

Reaction equation

HRID 1047541 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH2:30])[CH:28]=2)[N:23]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[N:22]=1.N1C=CC=CC=1>C(Cl)Cl>[NH:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]=[C:13]1[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[O:11])[CH:28]=2)[N:23]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[N:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5932582,4-Difluorophenyl isocyanateHCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

Product 1

HCID 136352253HCID 136352253, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Difluorophenyl isocyanate (10 mg, 0.064 mmol) was 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) and pyridine (0.02 mL, 0.177 mmol) in CH2Cl2 (5 mL), and the mixture was stirred for 24 h. The reaction mixture was filtered through Celite, and the solvent was removed in vacuo. Purification by flash chromatography (2% CH3OH/CH2Cl2) afforded the title compound (15 mg) as a solid. 1H NMR (400 MHz, CD3OD): δ 8.39 (s, 1H), 8.04 (m, 1H), 7.86 (m, 1H), 7.72 (m, 3H), 7.27 (m, 2H), 7.00 (m, 1H), 6.92 (m, 1H), 5.92 (dd, 1H, J=3.2 and 9.2 Hz), 4.02 (m, 1H), 3.85 (m, 1H), 2.67 (m, 1H), 2.14 (m, 1H), 1.71 (m, 1H), 1.28 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customPurification by flash chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-62b5391947a54f2f926d81cfe1b46947
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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