Sodium Bicarbonate → 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-(3-oxo-2,2-diphenylpropyl)picolinamide

HRID 1685340Notes

Reaction equation

HRID 1685340 reaction equation
[O:1]1CCO[CH:2]1[C:6]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:7][NH:8][C:9](=[O:31])[C:10]1[C:15]([F:16])=[C:14]([S:17][C:18]2[S:22][C:21]([NH:23][C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=3)=[N:20][CH:19]=2)[CH:13]=[CH:12][N:11]=1.C(=O)(O)[O-].[Na+]>CC(C)=O.O.C1COCC1.Cl>[F:16][C:15]1[C:10]([C:9]([NH:8][CH2:7][C:6]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:2]=[O:1])=[O:31])=[N:11][CH:12]=[CH:13][C:14]=1[S:17][C:18]1[S:22][C:21]([NH:23][C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=2)=[N:20][CH:19]=1

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 24957734N-(2-(1,3-dioxolan-2-yl)-2,2-diphenylethyl)-3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide

Product 1

HCID 592004433-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-(3-oxo-2,2-diphenylpropyl)picolinamideYield 104.3%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(2-(1,3-dioxolan-2-yl)-2,2-diphenylethyl)-3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide (0.248 g, 0.4040 mmol, described in Example 50) in acetone (10 mL), water (5 mL), THF (5 mL) and conc. HCl (1 mL) was heated at gentle reflux for 10 hours. The reaction was then neutralized with aq. sat. sodium bicarbonate and the volatiles were evaporated. The solid was collected by filtration and vacuum dried to give the crude title material (0.240 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 2.30 (3H, s), 4.27 (2H, d, J=6.32 Hz), 6.83 (1H, d, J=4.55 Hz), 6.89 (1H, s), 7.03 (1H, t, J=5.31 Hz) 7.22 (4H, d, J=7.07 Hz) 7.31-7.37 (2H, m), 7.40 (4H, t, J=7.33 Hz) 7.77 (1H, s), 8.15 (1H, d, J=5.05 Hz), 8.19 (1H, d, J=5.05 Hz), 8.28 (1H, t, J=6.19 Hz). 9.99 (1H, s) 11.82 (1H, s).

Workup

  1. temperatureat gentle reflux for 10 hours
  2. customthe volatiles were evaporated
  3. filtrationThe solid was collected by filtration and vacuum
  4. customdried

Sources & evidence

ORD record
ord-bc717a76aa4b49a99468a1ee7c9e39cd
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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