3-Amino-1-methylpyrrolidin-2-one → 4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]-N-(1-methyl-2-oxopyrrolidin-3-yl)benzamide

HRID 1520059Notes

Reaction equation

HRID 1520059 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[CH:14]=2)=[N:2]1.[NH2:24][CH:25]1[CH2:29][CH2:28][N:27]([CH3:30])[C:26]1=[O:31]>C(#N)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:24][CH:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])=[O:21])=[CH:22][CH:23]=3)[CH:14]=2)=[N:2]1

Participants

4

Reactant 2

HCID 457911333-Amino-1-methylpyrrolidin-2-oneHCID 679811434-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

Product 1

HCID 680609184-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]-N-(1-methyl-2-oxopyrrolidin-3-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was obtained following procedure described for example 26, but starting from 4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid (100 mg; 0.33 mmol; 1.0 eq.) and 3-amino-1-methylpyrrolidin-2-one (Chem Bridge Corp., 56 mg, 0.49 mmol, 1.5 eq.). The crude obtained was suspended in acetonitrile, filtered and dried to afford the title compound as a beige powder. 1H NMR (300 Mz, DMSO-d6) δ 13.38 (s, 1H), 9.43 (s, 1H), 8.94 (d, J=8.4 Hz, 1H), 8.36 (d, J=8.1 Hz, 1H), 8.21 (d, J=8.8 Hz, 2H), 8.11 (d, J=8.8 Hz, 2H), 7.61 (d, J=8.4 Hz, 1H), 7.50-7.38 (m, 1H), 7.31-7.15 (m, 1H), 4.74-4.52 (m, 1H), 3.42-3.32 (m, 2H), 2.77 (s, J=7.8 Hz, 3H), 2.44-2.27 (m, 1H), 2.13-1.85 (m, 1H). HPLC (Condition A): Rt 2.69 min (purity 92.2%). MS (ESI+): 402.3, MS (ESI−): 400.3.

Workup

  1. customThe crude obtained
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-d2c949a8493149dc8fe419fc85e1111a
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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