Water → 3-(5-(Pyrrolidin-1-ylmethyl)thiophen-2-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 629056노트

반응식

HRID 629056 반응식
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].CC1(C)C(C)(C)OB([C:30]2[S:34][C:33]([CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:32][CH:31]=2)O1.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[N:36]1([CH2:35][C:33]2[S:34][C:30]([C:2]3[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=3)[C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)=[O:6])=[CH:31][CH:32]=2)[CH2:37][CH2:38][CH2:39][CH2:40]1

참가 물질

6

반응물 3

HCID 962WaterHCID 13710333-bromo-N-(4-(trifluoromethoxy)phenyl)benzamideHCID 467397461-((5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)pyrrolidine

생성물 1

HCID 722028813-(5-(Pyrrolidin-1-ylmethyl)thiophen-2-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

3-Bromo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 3.1, 50 mg, 0.139 mmol), 1-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)pyrrolidine (0.180 mmol), (Ph3P)4Pd (8 mg, 6.94 μmol) 2 M Na2CO3 (0.104 mL, 0.208 mmol), water (0.8 mL) and DME (2.4 mL) were added to a vial, which was sealed and subjected to MW irradiation at 150° C. for 600 sec (very high absorbance). The RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL), the cartridge was washed with MeOH (10 mL) and the combined filtrates were evaporated under reduced pressure to give the crude product was purified by preparative HPLC to afford the title compound. UPLC-MS (Condition 6) tR=1.92 min, m/z=447.4 [M+H]+.

후처리

  1. customwas sealed
  2. customsubjected to MW irradiation at 150° C. for 600 sec (very high absorbance)
  3. filtrationThe RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL)
  4. washthe cartridge was washed with MeOH (10 mL)
  5. customthe combined filtrates were evaporated under reduced pressure
  6. customto give the crude product
  7. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-99397f261b8d4efb93a0bb75046519cc
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315489B2

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