Methanol → HCID 178434247, compound

HRID 598833Notes

Reaction equation

HRID 598833 reaction equation
I[C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[CH3:16])=[CH:5][N:6]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN1C(=O)CCC1.CO>C(Cl)Cl>[CH2:17]([NH:24][C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[CH3:16])=[CH:5][N:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 13387N-methyl-2-pyrrolidoneHCID 178434246HCID 178434246, compound2×

Product 1

HCID 178434247HCID 178434247, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
165 °C

Procedure

The title compound was prepared from 5-(2-iodooxazol-5-yl)-3-methyl-1H-indazole, Scheme 5. A glass microwave reaction vessel was charged with 5-(2-iodooxazol-5-yl)-3-methyl-1H-indazole (0.050 g, 154 μmol), benzyl amine (0.120 mL, 1100 μmol) and NMP (1.0 mL). The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 165° C. for 10 minutes. The obtained product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 1% to 10% 2 M NH3.MeOH in DCM, to give the title compound (14 mg, 30% yield) LCMS (API-ES) m/z (%): 305 (100%, M++H); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.69 (s, 1H) 7.48 (dd, J=8.72, 1.40 Hz, 1H) 7.42 (d, J=8.72 Hz, 1H) 7.38 (m, 2H) 7.31 (m, 2H) 7.22 (m, 1H) 7.14 (s 1H) 4.44 (s, 2H).

Workup

  1. customA glass microwave reaction vessel
  2. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  3. washeluting with a gradient of 1% to 10% 2 M NH3

Sources & evidence

ORD record
ord-e444438eb5c043ab9b2cc0772d678e61
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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