4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → HCID 67529791, compound

HRID 219929Notes

Reaction equation

HRID 219929 reaction equation
[NH2:1][C:2](=[N:19][OH:20])[C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:5]([F:18])[CH:4]=1.[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][N:23]1[C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=O)=[CH:30][C:29]=1[C:37]([F:40])([F:39])[F:38]>>[F:18][C:5]1[CH:4]=[C:3]([C:2]2[N:1]=[C:32]([C:31]3[CH:35]=[CH:36][C:28]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]4[CH3:21])=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:30]=3)[O:20][N:19]=2)[CH:17]=[CH:16][C:6]=1[O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10]

Participants

3

Reactant 2

HCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acidHCID 72307490Tert-butyl {4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}acetate

Product 1

HCID 67529791HCID 67529791, compound

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 49 (142.14 mg; 0.50 mmol) and Intermediate 15 (172.37 mg; 0.60 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5), affording the title compound as a white solid. LC/MS (Method B): 536.4 (M+H)+. HPLC (Method A) Rt 7.2 min (Purity: 99.4%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5)

Sources & evidence

ORD record
ord-4f3c505b3c47498b8875b7357d255eb1
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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