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Water → HCID 67516775, 화합물

HRID 919619
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HRID 919619 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH3:19])[CH:15]([NH:20][C:21]3[C:22]4[CH:29]=[CH:28][N:27](S(C5C=CC(C)=CC=5)(=O)=O)[C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[N:24]1[C:23]2[NH:27][CH:28]=[CH:29][C:22]=2[C:21]([NH:20][CH:15]2[CH:16]([CH3:19])[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][NH:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:14]2)=[N:26][CH:25]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86706478HCID 86706478, 화합물

생성물 1

HCID 67516775HCID 67516775, 화합물수율 27.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 2-(3,5-dichlorophenylamino)-1-(4-methyl-3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)ethanone (100 mg, 0.17 mmol) in MeOH:H2O (4:1 mL) was added K2CO3 (94 mg, 0.68 mmol) and the reaction mixture was heated to 60° C. for 1 h. The reaction mixture was concentrated in vacuo and the residue obtained was diluted in EtOAc (50 mL). The EtOAc suspension was filtered through celite, the filtrate was dried over Na2SO4, and concentrated in vacuo to give a residue that was subjected to purification by column chromatography (silica gel, gradient MeOH in DCM) to afford the titled intermediate (20 mg, 27%). 1H NMR (400 MHz, DMSO-d6): δ 11.61-11.45 (m, 1H), 8.19-8.06 (m, 1H), 7.08-6.43 (m, 5H), 6.22-6.15 (m, 1H), 4.59-4.21 (m, 2H), 4.15-3.75 (m, 3H), 3.25-2.98 (m, 2H), 2.78-2.45 (m, 1H), 2.15-1.99 (m, 1H), 1.86-1.7-62 (m, 2H), 0.98-0.77 (m, 3H). LC-MS: m/z [M+1]=433.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. filtrationThe EtOAc suspension was filtered through celite
  4. dry with materialthe filtrate was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue that
  7. customwas subjected to purification by column chromatography (silica gel, gradient MeOH in DCM)

출처 및 근거

ORD 기록
ord-5e7f282a1b924f9bb8b0cc62d0df86e4
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273028B2

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