tert-Butyl 4-chloropicolinate → HCID 178450754, compound

HRID 572238Notes

Reaction equation

HRID 572238 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]2)=[O:10])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].Cl[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:25]=1.CC(C)([O-])C.[K+]>C1COCC1>[C:33]([O:32][C:30]([C:26]1[CH:25]=[C:24]([O:18][C@H:15]2[CH2:14][CH2:13][C@@H:12]([NH:11][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:19]([F:20])([F:21])[F:22])[CH:4]=3)=[O:10])[CH2:17][CH2:16]2)[CH:29]=[CH:28][N:27]=1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 11806045tert-Butyl 4-chloropicolinateHCID 23665647Potassium tert-butoxideHCID 178522078HCID 178522078, compound

Product 1

HCID 178450754HCID 178450754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cis-1-(4-chloro-3-trifluoromethyl-phenyl)-3-(4-hydroxy-cyclohexyl)-urea (0.38 g, 1.13 mmol) and tert-butyl 4-chloropicolinate (0.24 g, 1.13 mmol) in THF (12 mL) was added 1.0 M potassium tert-butoxide solution in THF (3.4 mL, 3.4 mmol) at 0° C. The reaction mixture was allowed to slowly warm to room temperature and then stirred overnight. The reaction was quenched by adding water and the resulting white precipitates were collected and washed with water. Purification by column chromatography (6:4 Hexanes-EtOAc) gave the title compound, 0.32 g (55%) as a yellowish powder. 1H NMR (300 MHz, DMSO-d δ 8.78 (s, 1H), 8.48 (d, J=6 Hz, 1H), 8.09-8.06 (m, 1H), 7.55-7.50 (m, 2H), 7.46 (d, J=2 Hz, 1H), 7.21 (dd, J=6 and 2 Hz, 1H), 6.48 (d, J=8 Hz, 1H), 4.82-4.67 (m, 1H), 3.75-3.59 (m, 1H), 1.91-1.47 (m, 17H).

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. customthe resulting white precipitates
  4. customwere collected
  5. washwashed with water
  6. customPurification by column chromatography (6:4 Hexanes-EtOAc)

Sources & evidence

ORD record
ord-ed78060f6c0d4f97945ee53646fdd496
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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