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Methyl 4-chloroanthranilate → HCID 11754542, 화합물

HRID 225772
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HRID 225772 반응식
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CO[C:48](=O)[C:49]1[CH:54]=[CH:53][C:52](Cl)=[CH:51][C:50]=1[NH:56][C:57]([CH:59]1[CH2:64][CH2:63][CH2:62][CH2:61][N:60]1[C:65](=[O:73])[C:66]1[CH:71]=[CH:70][C:69]([CH3:72])=[CH:68][CH:67]=1)=O>CN(C=O)C>[CH2:50]([N:56]1[C:3](=[O:12])[C:4]2[C:5](=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=2)[N:11]=[C:57]1[CH:59]1[CH2:64][CH2:63][CH2:62][CH2:61][N:60]1[C:65](=[O:73])[C:66]1[CH:71]=[CH:70][C:69]([CH3:72])=[CH:68][CH:67]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:48]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 80001Methyl 4-chloroanthranilateHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 69063202HCID 69063202, 화합물

생성물 1

HCID 11754542HCID 11754542, 화합물수율 21%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

In an ice bath at −15° C., pure compound of Formula 202 (7.2 g, 29 mmol) was combined with 2-amino-4-chloro-benzoic acid methyl ester (4.5 g, 24 mmol), PyBroP (2.3 g, 4.9 mmol) and diisopropylethylamine (0.95 mL, 5.4 mmol) in DMF (30 mL). The resulting mixture was stirred ovemight, allowing the temperature to rise to room temperature with the bath. The solution was concentrated under vacuum and the residue partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with water (3×100 mL) and concentrated under vacuum. The resulting residue was purified by silica gel chromatography using 40% ethyl acetate/hexanes as eluent to give 2.66 g (21% yield) of the desired product of Formula 203, 4-chloro-2-{[1-(4-methyl-benzoyl)-piperidine-2-carbonyl]amino}-benzoic acid methyl ester, as a crystalline solid. LRMS (MH+) m/z 472.

후처리

  1. customto rise to room temperature with the bath
  2. concentrationThe solution was concentrated under vacuum
  3. customthe residue partitioned between ethyl acetate (200 mL) and water (200 mL)
  4. washThe organic layer was washed with water (3×100 mL)
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-54f87a778ce448d29bfe294692fd351c
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557115B2

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