Lithium hydroxide, monohydrate → Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-4-fluorophenyl)acetate

HRID 1779015ノート

反応式

HRID 1779015 の反応式
O[Li:2].O.[F:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:43][C:44]([O:46]C)=[O:45])=[C:9]([CH:42]=1)[CH2:10][CH2:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[N:13]=1>O.C1COCC1>[C:38]([O:37][C:35]([N:32]1[CH2:31][CH2:30][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:42]=[C:5]([F:4])[CH:6]=[CH:7][C:8]=4[CH2:43][C:44]([O-:46])=[O:45])[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][N:15]=3)=[CH:28][CH:27]=2)[CH2:34][CH2:33]1)=[O:36])([CH3:41])([CH3:39])[CH3:40].[Li+:2]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712666tert-Butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

生成物 1

HCID 86712667Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-4-fluorophenyl)acetate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

LiOH.H2O (0.063 g, 1.5 mmol) was added to a stirred solution of tert-butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A52) (0.092 g, 0.15 mmol) in H2O (0.5 mL) and THF (5 mL) and the resulting mixture heated at 40° C. overnight. The volatiles were removed in vacuo and the residue was taken up in DCM (50 mL). The resulting solution was washed with saturated aqueous Na2CO3 (25 mL) then the aqueous phase was then extracted with DCM (2×25 mL). The organic layers were combined, dried over MgSO4 and the volatiles were removed in vacuo to yield the title compound A53 (0.089 g, 98%); LCMS-A: rt 6.596 min; m/z 603 [(M-Li)+H]+.

後処理

  1. customThe volatiles were removed in vacuo
  2. washThe resulting solution was washed with saturated aqueous Na2CO3 (25 mL)
  3. extractionthe aqueous phase was then extracted with DCM (2×25 mL)
  4. dry with materialdried over MgSO4
  5. customthe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-cbfe8206618b44b69c87de8e00994969
出典データセット
uspto-grants-2016_02
特許番号
US09266864B2

反応ノート

読み込み中…