Pyrazole → HCID 89657434, compound

HRID 930851Notes

Reaction equation

HRID 930851 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([C:9]2[C:10]3[CH:19]=[CH:18][NH:17][C:11]=3[C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)[CH:8]=1.[NH:27]1[CH:31]=[CH:30][CH:29]=[N:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH3:15][N:13]1[CH:14]=[C:9]([C:7]2[CH:8]=[C:3]([CH2:2][N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)[CH:4]=[CH:5][C:6]=2[O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:10]2[CH:19]=[CH:18][NH:17][C:11]=2[C:12]1=[O:16]

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 716160564-[5-(hydroxymethyl)-2-phenoxyphenyl]-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Product 1

HCID 89657434HCID 89657434, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 20b (0.04 g, 0.115 mmol), 1H-pyrazole (0.016 g, 0.231 mmol), and triphenylphosphine (0.061 g, 0.231 mmol) in tetrahydrofuran (1 mL) was stirred for 2 minutes. To this solution was added di-t-butyl azodicarboxylate (DTBAD, 0.053 g, 0.231 mmol). The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, and the residue was purified by preparative HPLC (C18, 10-80% acetonitrile/water with 0.1% TFA) to afford 0.006 g of the title compound. 1H NMR (500 MHz, DMSO-d6) δ 3.49 (s, 3H), 5.37 (s, 2H), 5.21 (t, J=5.8 Hz, 1H), 6.17-6.18 (m, 1H), 6.28 (t, J=1.98 Hz, 1H), 6.86 (d, J=7.63 Hz, 2H), 6.97 (d, J=8.24 Hz, 1H), 7.02 (t, J=7.32 Hz, 4H), 7.22-7.29 (m, 5H), 7.39 (d, J=2.14 Hz, 1H), 7.47 (d, J=1.83 Hz, 1H), 7.53-7.46 (m, 3H), 7.86 (d, J=2.44 Hz, 1H), 11.97 (s, 1H). (ESI+) m/z 397.2 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC (C18, 10-80% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-b05b5f4b75694b3aa78ba8c0b18a9f1a
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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