HCID 11209094, compound → HCID 11300491, compound

HRID 1592964Notes

Reaction equation

HRID 1592964 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O>CO>[C:17]1([CH:15]([C:12]2[S:13][CH:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)[N:11]=2)[CH3:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 11209094HCID 11209094, compound

Product 1

HCID 11300491HCID 11300491, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-nitrophenyl)-2-(1-phenylethyl)-1,3-thiazole (1-5, 0.13 g, 0.42 mmol) was dissolved in anhydrous MeOH (5.0 mL) and deoxygenated under vacuum. 10% Pd/C (0.02 g) was added and the reaction was purged with an H2 baloon. The vigorously stirred reaction was kept under H2 for 12 h, and then filtered through celite. The reaction was then concentrated and subjected to reverse phase HPLC (C-8, 5-95% MeOH—H2O w/0.1% TFA) to provide pure 4-[2-(1-phenylethyl)-1,3-thiazol-4-yl]aniline (4-1). 1H NMR (300 MHz, CDCl3) δ 8.20 (d, J=8.6 Hz, 2H), 7.71 (s, 1H), 7.38 (d, J=8.7 Hz, 2H), 7.34 (d, J=7.8 Hz, 2H), 7.32 (dd, J=7.8, 7.3 Hz, 2H), 7.24 (dd, J=7.3, 7.1 Hz, 1H), 5.01 (br s, 2H), 4.52 (q, J=7.1 Hz, 1H), 1.79 (d, J=7.1 Hz, 3H); MS 281.0 found 281.4 (M+H+) required.

Workup

  1. customdeoxygenated under vacuum
  2. addition10% Pd/C (0.02 g) was added
  3. customthe reaction was purged with an H2 baloon
  4. customThe vigorously stirred reaction
  5. filtrationfiltered through celite
  6. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-166b64e67017446b8ebc3c097b2c5221
Source dataset
uspto-grants-2007_11
Patent number
US07294640B2

Reaction notes

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