Triphenylphosphine → 1-[4-(Aminocarbonyl)-6-chloro-2-pyridinyl]-4-piperidinyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233955노트

반응식

HRID 2233955 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[N:10]=1)[C:5]([NH2:7])=[O:6].[Br:18][C:19]1[CH:20]=[C:21]([C:25](O)=[O:26])[NH:22][C:23]=1[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:18][C:19]1[CH:20]=[C:21]([C:25]([O:17][CH:14]2[CH2:15][CH2:16][N:11]([C:9]3[CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=[C:2]([Cl:1])[N:10]=3)[CH2:12][CH2:13]2)=[O:26])[NH:22][C:23]=1[CH3:24]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 685182224-Bromo-5-methyl-1H-pyrrole-2-carboxylic acid2회HCID 860383812-Chloro-6-(4-hydroxypiperidin-1-yl)isonicotinamide2회

생성물 1

HCID 866083101-[4-(Aminocarbonyl)-6-chloro-2-pyridinyl]-4-piperidinyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate수율 5.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

2-chloro-6-(4-hydroxypiperidin-1-yl)isonicotinamide (Intermediate 62; 123 mg, 0.48 mmol), 4-bromo-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 18) (98 mg, 0.48 mmol) and triphenylphosphine (138 mg, 0.53 mmol) were stirred in anhydrous THF and cooled to 0° C. DEAD (83 μl, 0.53 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was filtered, diluted with EtOAc and washed with water and dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc/hexane (4:1) to afford the title compound (11 mg).

후처리

  1. filtrationThe mixture was filtered
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography
  7. washeluting with EtOAc/hexane (4:1)

출처 및 근거

ORD 기록
ord-ea6c5af72e6d4271ba187d29b02a0df9
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

반응 노트

불러오는 중…