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

HRID 1685340ノート

反応式

HRID 1685340 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-bc717a76aa4b49a99468a1ee7c9e39cd
出典データセット
uspto-grants-2012_04
特許番号
US08148400B2

反応ノート

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