Pyridine → HCID 136352256, compound

HRID 1047546Notes

Reaction equation

HRID 1047546 reaction equation
[CH:1]1([N:4]=[C:5]=[O:6])[CH2:3][CH2:2]1.[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([NH2:25])[CH:23]=2)[N:18]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[N:17]=1.N1C=CC=CC=1>C(Cl)Cl>[NH:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:7]=[C:8]1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([NH:25][C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:6])[CH:23]=2)[N:18]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[N:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 637659IsocyanatocyclopropaneHCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

Product 1

HCID 136352256HCID 136352256, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopropylisocyanate (4 g, 0.048 mmol) was added to a solution of 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (15 mg, 0.045 mmol) and pyridine (0.01 mL, 0.126 mmol) in CH2Cl2 (5 mL). The mixture was stirred for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (2% CH3OH/CH2Cl2) afforded the title compound (10 mg) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 7.93 (d, 1H, J=8.8 Hz), 7.83 (m, 1H), 7.49 (d, 1H, J=8.8 Hz), 7.27-7.24 (m, 2H), 7.17 (s, 1H), 5.71 (dd, 1H, J=2.4 and 9.2 Hz), 4.04 (m, 1H), 3785 (m, 1H), 2.59 (m, 2H), 2.17-2.07 (m, 2H), 1.74 (m, 5H), 0.84 (q, 2H, J=5.2 Hz).

Workup

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

Sources & evidence

ORD record
ord-223a9deade0341fcb829a5b1386c58c3
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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