Water → HCID 67436467, compound

HRID 1496636Notes

Reaction equation

HRID 1496636 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:5]=[CH:4][N:3]=1.O.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>>[CH:23]1([NH:26][C:2]2[CH:7]=[C:6]([C:8]3[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=3[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:5]=[CH:4][N:3]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 962WaterHCID 69828CyclopropylamineHCID 156034394-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]-2-fluoropyridine

Product 1

HCID 67436467HCID 67436467, compound

Conditions

Temperature
150 °C

Procedure

In a closed vessel, 600 mg (1.98 mmol) of 2-fluoro-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine (described, for example, in J. Med. Chem, 2005, 48, 5966-5979) in 10 ml cyclopropylamine are heated with stirring at 150° C. After 16 h, the reaction mixture is stirred into 100 ml of water and extracted with ethyl acetate (3×50 ml). The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. The residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 520 mg (77%) of the desired product; 1H-NMR(DMSO-d6) δ: 7.96 (d, 1H), 7.52 (m, 2H), 7.17 (m, 2H), 6.65 (s, 1H), 6.49 (s 1H), 6.45 (d, 1H), 3.04 (q, 2H), 2.37 (m, 1H), 1.36 (t, 3H), 0.55 (m, 2H), 0.33 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. customThe residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-a287f6e278f54415a1aec4acb0dd3af5
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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