2-Amino-4-(benzyloxy)benzamide → HCID 66610642, 화합물

HRID 1801921노트

반응식

HRID 1801921 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[O:30]C(=O)[O:28][C:27]2=O)=[CH:22][CH:21]=1>C1COCC1>[CH2:12]([O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([NH:1][C:27](=[O:28])[CH:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[OH:30])[CH:10]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 231302772-Amino-4-(benzyloxy)benzamideHCID 866490505-(4-Fluorophenyl)-1,3-dioxolane-2,4-dione

생성물 1

HCID 66610642HCID 66610642, 화합물수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
63 °C

실험 절차

To a solution of 2-amino-4-(benzyloxy)benzamide (4.0 g, 16.5 mmol) in THF (60 mL) was added a solution of 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione (3.65 g, 18.6 mmol) from Example 16 in THF (20 mL) portionwise at rt. After heating to 63° C. for 18 h, the solution was cooled and concentrated. After addition of H2O, the solution was extracted twice with DCM. The combined organic phases were washed with brine and dried over sodium sulfate. Chromatography on silica gel eluting with 10 to 80% EtOAc/DCM afforded 4-(benzyloxy)-2-(2-(4-fluorophenyl)-2-hydroxyacetamido)benzamide as a foamy solid (4.1 g, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm 5.06 (m, 1H), 5.12 (s, 2 H) 6.68-6.74 (m, 1H) 7.14-7.20 (m, 2 H) 7.32-7.51 (m, 6 H) 7.77 (d, J=8.85 Hz, 1 H) 8.05 (br. s., 1 H) 8.30 (d, J=2.64 Hz, 1 H) 12.73 (s, 1 H). LC-MS (ESI) m/z 392 (M−2).

후처리

  1. temperaturethe solution was cooled
  2. concentrationconcentrated
  3. additionAfter addition of H2O
  4. extractionthe solution was extracted twice with DCM
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-cb5265324db942ee8a77fd972607d681
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349851B2

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