Trifluoroacetic acid → Trifluoroacetic acid

HRID 530834Notes

Reaction equation

HRID 530834 reaction equation
COC1C=CC(C[N:8]([CH2:30][C:31]2[N:32]=[N:33][N:34]([CH3:36])[CH:35]=2)[C:9]2[C:10](=[O:29])[N:11]([CH3:28])[N:12]=[C:13]([O:15][CH2:16][C@H:17]3[CH2:19][C@@H:18]3[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)[CH:14]=2)=CC=1.C([O-])(O)=O.[Na+].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C@H:18]2[CH2:19][C@@H:17]2[CH2:16][O:15][C:13]2[CH:14]=[C:9]([NH:8][CH2:30][C:31]3[N:32]=[N:33][N:34]([CH3:36])[CH:35]=3)[C:10](=[O:29])[N:11]([CH3:28])[N:12]=2)=[N:21][CH:22]=1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90419149HCID 90419149, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 117610241HCID 117610241, compound

Procedure

A solution of 4-((4-methoxybenzyl)((1-methyl-1H-1,2,3-triazol-4-yl)methyl)amino)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (55 mg, 0.11 mmol) in TFA (2 mL) was stirred at room temperature for 2 h, then pH was adjusted to 7˜8 with saturated NaHCO3 solution. Extracted with EtOAc (20 mL*3), washed with H2O and brine, and concentrated. The residue was purified by Prep-HPLC (CH3CN in 0.05% TFA/H2O 30-95% v/v as mobile phase) to give title compound as a TFA salt, the structure was confirmed by NOE. ESI-MS: 398.2 (M+H)+. 1H NMR (400 MHz, MeOD) δ 8.34 (d, 1H), 8.03 (dd, 1H), 7.86 (s, 1H), 7.80 (d, 1H), 5.88 (s, 1H), 4.47 (s, 2H), 4.30 (dd, 1H), 4.11 (dd, 1H), 4.06 (s, 3H), 4.01 (s, 3H), 3.62 (s, 3H), 2.36-2.32 (m, 1H), 2.01-1.96 (m, 1H), 1.41-1.41 (m, 2H).

Workup

  1. extractionExtracted with EtOAc (20 mL*3)
  2. washwashed with H2O and brine
  3. concentrationconcentrated
  4. customThe residue was purified by Prep-HPLC (CH3CN in 0.05% TFA/H2O 30-95% v/v as mobile phase)

Sources & evidence

ORD record
ord-452bea1b663a4ccd8678638ec4ffc39f
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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