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 1692358노트

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HRID 1692358 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e86f528a4a6c4f0bb46acbe5651411c2
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153814B2

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