Hexachloroethane → 6-Fluoro-3-(4-methyl-3-triisopropylsilanyloxymethyl-piperazin-1-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 2282471노트

반응식

HRID 2282471 반응식
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[F:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][NH:17][C:18](=O)[CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH:22]([CH2:27][O:28][Si:29]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[CH2:21]2)=[N:14][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>C1COCC1>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:18]([CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH:22]([CH2:27][O:28][Si:29]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[CH2:21]3)=[N:17][N:16]=2)[CH:15]=1

참가 물질

6

반응물 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687052(4-Methyl-3-triisopropylsilanyloxymethyl-piperazin-1-yl)-acetic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

생성물 1

HCID 866870556-Fluoro-3-(4-methyl-3-triisopropylsilanyloxymethyl-piperazin-1-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridine수율 60.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Hexachloroethane (426 mg, 1.80 mmol) was added portion-wise to a stirred mixture of Intermediate 56c (410 mg, 0.90 mmol), Ph3P (472 mg, 1.80 mmol) and Et3N (500 μL, 3.60 mmol) in THF (15 mL) at RT. The reaction mixture was stirred for 18 h, then filtered and concentrated in vacuo. The resulting residue was purified by FCC, using 0-25% MeOH in EtOAc, to give the title compound (237 mg, 60%). LCMS (Method 3): Rt 2.95 min, m/z 436 [MH+].

후처리

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by FCC

출처 및 근거

ORD 기록
ord-d570bbd734e74bdcb1d4ad1216c107ba
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139584B2

반응 노트

불러오는 중…