3-Methyl-4-(4-methylthiophen-3-yl)benzoic acid → HCID 67528391, compound

HRID 219910Notes

Reaction equation

HRID 219910 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:15]([CH3:16])=[CH:14][S:13][CH:12]=1)[C:5]([OH:7])=O.[NH2:17][C:18](=[N:30]O)[C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1[F:29]>>[F:29][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:19]=1[C:18]1[N:17]=[C:5]([C:4]2[CH:8]=[CH:9][C:10]([C:11]3[C:15]([CH3:16])=[CH:14][S:13][CH:12]=3)=[C:2]([CH3:1])[CH:3]=2)[O:7][N:30]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

3

Reactant 2

HCID 579938003-Methyl-4-(4-methylthiophen-3-yl)benzoic acidHCID 72307476Methyl 4-[amino(hydroxyimino)methyl]-3-fluorobenzoate

Product 1

HCID 67528391HCID 67528391, compound

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 6 (116.2 mg; 0.50 mmol) and Intermediate 2 (106.1 mg; 0.50 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 suspended in ACN, filtrated and washed with cHex dried under vacuo, affording the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 8.35-8.30 (m, 1H), 8.17 (d, J=1.3 Hz, 1H), 8.08-8.01 (m, 2H), 7.95 (dd, J=11.0, 1.3 Hz, 1H), 7.46-7.42 (m, 2H), 7.35 (dd, J=3.2, 1.1 Hz, 1H), 3.93 (s, 3H), 2.24 (s, 3H), 2.01 (s, 3H). LC/MS (Method B): 409.1 (M+H)+. HPLC (Method A) Rt 6.06 min (Purity: 93.6%).

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. filtrationfiltrated
  7. washwashed with cHex
  8. customdried under vacuo

Sources & evidence

ORD record
ord-110ebf61def34e53b14c83ddc4ead055
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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