Sodium Bicarbonate → tert-Butyl [(4-{2-[2-(azetidin-1-ylmethyl)pyridin-4-yl]-4-chlorophenoxy}-2,5-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate

HRID 46393ノート

反応式

HRID 46393 の反応式
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[C:12]([F:13])=[CH:11][C:10]([S:14]([N:17]([C:25]3[N:26]=[CH:27][S:28][CH:29]=3)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:16])=[O:15])=[C:9]([F:30])[CH:8]=2)=[C:4]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([CH:39]=O)[CH:34]=2)[CH:3]=1.Cl.[NH:42]1[CH2:45][CH2:44][CH2:43]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[N:42]1([CH2:39][C:35]2[CH:34]=[C:33]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:32]=[CH:31][C:5]=3[O:6][C:7]3[C:12]([F:13])=[CH:11][C:10]([S:14]([N:17]([C:25]4[N:26]=[CH:27][S:28][CH:29]=4)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])(=[O:16])=[O:15])=[C:9]([F:30])[CH:8]=3)[CH:38]=[CH:37][N:36]=2)[CH2:45][CH2:44][CH2:43]1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 59436611tert-Butyl ({4-[4-chloro-2-(2-formylpyridin-4-yl)phenoxy]-2,5-difluorophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate

生成物 1

HCID 59436494tert-Butyl [(4-{2-[2-(azetidin-1-ylmethyl)pyridin-4-yl]-4-chlorophenoxy}-2,5-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl ({4-[4-chloro-2-(2-formylpyridin-4-yl)phenoxy]-2,5-difluorophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate, (Preparation 879, 0.36 g, 0.00059 mol) was dissolved in dichloromethane (3 mL) then azetidine hydrochloride (0.083 g, 0.00089 mol) was added and reaction allowed to stir at room temperature for 30 minutes. Sodium triacetoxyborohydride (0.144 g, 0.00068 mol) was added and the reaction stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate solution (5 mL) was added and the reaction stirred for 30 minutes. The reaction was then passed through a phase separation cartridge and the isolated dichloromethane layer concentrated in vacuo to give the desired product as an orange foam (0.325 g.

後処理

  1. customreaction
  2. stirringthe reaction stirred at room temperature for 18 hours
  3. stirringthe reaction stirred for 30 minutes
  4. customThe reaction was then passed through a phase separation cartridge
  5. concentrationthe isolated dichloromethane layer concentrated in vacuo

出典と根拠

ORDレコード
ord-9f696dac1e7a468aa1a120d512059ce7
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

反応ノート

読み込み中…