Triethylamine → 2-tert-Butyl-4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)propyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2422097

반응식

HRID 2422097 반응식
[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].C(C(C(C(O)=O)O)O)(O)=O.[CH3:30][C:31]1[CH:35]=[C:34]([CH3:36])[N:33]([CH2:37][CH2:38][CH2:39][NH2:40])[N:32]=1.C(N(CC)CC)C>CC#N>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:40][CH2:39][CH2:38][CH2:37][N:33]2[C:34]([CH3:36])=[CH:35][C:31]([CH3:30])=[N:32]2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 45074855HCID 45074855, 화합물HCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

생성물 1

HCID 672433062-tert-Butyl-4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)propyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide수율 94%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (150 mg, 0.5 mmol), 3-(3,5-dimethyl-pyrazol-1-yl)-propylamine tartrate (167 mg, 0.55 mmol) were mixed in MeCN (3 ml). Triethylamine (0.23 ml, 1.65 mmol) was added and the mixture was heated in a microwave reactor at 120° C. for 15 mins. The reaction mixture was evaporated to dryness and the residue was purified by column chromatography (ISOLUTE SI, 20 g/70 ml), eluting with DCM and then MeOH/DCM (1:99), to give the title compound (195 mg, 94%). 1H NMR (400 MHz, CDCl3): δ 1.70 (s, 9H), 1.72-1.79 (m, 2H), 2.05 (s, 3H), 2.18 (s, 3H), 2.81-2.86 (m 2H), 3.79 (t, 2H), 5.71 (bs, 2H), 7.37-7.46 (m, 5H); 13C NMR (100 MHz, CDCl3): δ 10.8, 13.4, 27.5, 29.2, 41.5, 45.4, 61.3, 105.1, 106.8, 125.0, 128.4, 129.4, 131.4, 135.0, 138.5, 147.7, 159.3; Mass Spectrum: M+H+ 417.

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was purified by column chromatography (ISOLUTE SI, 20 g/70 ml)
  3. washeluting with DCM

출처 및 근거

ORD 기록
ord-f461b85ca3e34b0b93aa481480ceddd1
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960380B2

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