Chloroacetyl chloride → HCID 86708103, 화합물

HRID 1497776

반응식

HRID 1497776 반응식
[NH2:1][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.CCN(C(C)C)C(C)C.[Cl:44][CH2:45][C:46](Cl)=[O:47]>C1COCC1>[Cl:44][CH2:45][C:46]([NH:1][C:2]1[N:34]=[C:5]2[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)=[C:7]([CH3:23])[C:8]([C:10]3[N:14]([C:15]4[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=4)[N:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1)=[O:47]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chloride2회HCID 81531DiisopropylethylamineHCID 730509764-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile

생성물 1

HCID 86708103HCID 86708103, 화합물수율 71.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-{5-[2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 1, 400 mg, 0.87 mmol) was stirred in dry THF (5 mL) and DIPEA (0.3 mL, 1.765 mmol) was added followed by the dropwise addition of chloroacetyl chloride (104 μL, 1.258 mmol). After 45 mins, a further quantity (69 μL) of chloroacetyl chloride was added and stirring was continued for 18 hrs. The reaction mixture was partitioned between EtOAc and water, the organic layer washed with saturated brine and then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography eluting with 65% EtOAc in cyclohexane to give title compound (334 mg).

후처리

  1. waitwas continued for 18 hrs
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. washthe organic layer washed with saturated brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by flash chromatography
  7. washeluting with 65% EtOAc in cyclohexane

출처 및 근거

ORD 기록
ord-90bf7f71a2664e0dae109cec6263c4a4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199984B2

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