2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → HCID 178494466, compound

HRID 400778Notes

Reaction equation

HRID 400778 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].O[N:21]=[C:22]([C:24]1[CH:32]=[C:31]([CH3:33])[C:27]2[NH:28][CH:29]=[N:30][C:26]=2[CH:25]=1)[NH2:23]>CCOCC>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:21]=[C:22]([C:24]3[CH:32]=[C:31]([CH3:33])[C:27]4[NH:28][CH:29]=[N:30][C:26]=4[CH:25]=3)[N:23]=2)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Participants

4

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 178426648HCID 178426648, compound

Product 1

HCID 178494466HCID 178494466, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Title compound was prepared following general procedure 2 starting from Intermediate 14 (308 mg; 1.2 mmol) and Intermediate 3 (228 mg; 1.2 mmol). The reaction mixture was diluted with Et2O, washed with water and brine and evaporated under vacuum. Purification by silica column chromatography (EtOAc/c-Hex, 30/70 to 70/30) afforded the title compound as a pink powder. 1H NMR (DMSO-d6) δ 12.92 (br s, 0.5H), 12.71 (br s, 0.5H), 8.38 (d, J=6.0 Hz, 1H), 8.34 (d, J=1.3 Hz, 1H), 8.26-8.12 (m, 2H), 7.80 (d, J=6.8 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 7.39-7.25 (m, 3H), 7.16 (d, J=7.0 Hz, 1H), 4.27-4.14 (m, 2H), 3.26 (s, 3H), 2.65 (s, 1.5H), 2.62 (s, 1.5H), 2.05 (s, 3H). LC/MS (method B): 409.3 (M−H)−; 411.3 (M+H)+. HPLC (Method A) Rt 4.11 min (Purity: 100.0%).

Workup

  1. customTitle compound was prepared
  2. washwashed with water and brine
  3. customevaporated under vacuum
  4. customPurification by silica column chromatography (EtOAc/c-Hex, 30/70 to 70/30)

Sources & evidence

ORD record
ord-57cd18b4ce2c4ab9bc86e8e1bec39579
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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