Acetic Acid → 3-(1-Methyl-piperidin-4-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 1807997

반응식

HRID 1807997 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[CH3:17][N:18]1[CH2:23][CH:22]=[C:21](O[Si](C)(C)C)[CH2:20][CH2:19]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClC(Cl)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1)=[O:4]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 100811201-Methyl-4-trimethylsilanyloxy-1,2,3,6-tetrahydro-pyridine

생성물 1

HCID 207757493-(1-Methyl-piperidin-4-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester수율 73%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a stirred solution of methyl-3-amino-5-phenylthiophene-carboxylate (233 mg, 1.0 mmol) and 1-methyl-4-trimethylsilanyloxy-1,2,3,6-tetrahydro-pyridine (370 mg, 2.0 mmol) in dichloroethane (3.0 mL) was added AcOH (0.114 mL, 2.0 eq) and followed addition of NaBH(OAc)3 (424 mg, 2.0 mmol) in one portion. The resultant reaction mixture was stirred at RT for weekend, aq. 10% NaOH (until basic) was added, after 30 min, reaction mixture was extracted with dichloromethane. The organic extract was washed with brine and dried. The crude product was purified on silica gel column using 20% EtOAc/hexane for unreacted starting material followed by CHCl3/MeOH/Et3N (180/16/1) furnished the 3-(1-methyl-piperidin-4-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (240 mg, 73%). NMR 1H (CDCl3, 400 MHz): 7.64-7.6 (m, 2H), 7.43-7.34 (m, 3H), 6.83 (brs, 2H), 3.83 (s, 3H), 3.46-3.4 (m, 1H), 2.82-2.74 (m, 1H), 2.3 (s, 3H), 2.26-2.2 (m, 4H), 1.72-1.62 (m, 2H).

후처리

  1. customThe resultant reaction mixture
  2. customreaction mixture
  3. extractionwas extracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with brine
  6. customdried
  7. customThe crude product was purified on silica gel column

출처 및 근거

ORD 기록
ord-8c539e10f72a412ebbcd3e3476afcca5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357718B2

연결된 노트

불러오는 중…