Triethylamine → HCID 59580853, compound

HRID 533302Notes

Reaction equation

HRID 533302 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9](C(O)=O)=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH:2]=1.CC[N:21]([CH2:24]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C1(C)C=CC=CC=1.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[C:50]([O:54][C:24](=[O:33])[NH:21][C:9]1[S:8][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:11][C:10]=1[C:12]([F:13])([F:14])[F:15])([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22595558Toluene tert-butyl alcoholHCID 59580876Pyridin-3-yl-4-trifluoromethyl-thiazole-5-carboxylic acid

Product 1

HCID 59580853HCID 59580853, compoundYield 59%

Procedure

To 2-pyridin-3-yl-4-trifluoromethyl-thiazole-5-carboxylic acid (6.33 g, 23.1 mmol) in toluene/tert-butyl alcohol (100 mL each) was added Et3N (3.21 mL, 23.1 mmol) and diphenyl phosphoryl azide (5 mL, 23.1 mmol). The reaction mixture was stirred at room temperature for 5 min and then heated at 95° C. for 4 h. The mixture was cooled to room temperature and the solvents were removed under reduced pressure. The crude product was purified by silica gel column chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as a white solid (4.7 g, 59%): mp 145-147° C.; 1H NMR (300 MHz, CDCl3) δ 9.11 (dd, J=2.5, 0.8 Hz, 1H), 8.67 (dd, J=5.0, 1.7 Hz, 1H), 8.22 (ddd, J=8.0, 2.5, 1.7 Hz, 1H), 7.58 (br s, 1H), 7.39 (ddd, J=8.0, 4.7, 0.8 Hz, 1H), 1.59 (s, 9H); ESIMS m/z 346.5 (M+1), m/z 344.2 (M−1).

Workup

  1. temperatureheated at 95° C. for 4 h
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by silica gel column chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-74ab4f7ad3594fc7bca9a2dd60243b38
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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