Formaldehyde → HCID 66919001, 화합물

HRID 2354217노트

반응식

HRID 2354217 반응식
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][NH:27]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.[CH2:32]=O>C(O)=O>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][N:27]5[CH3:32])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:2][CH2:3]1

참가 물질

4

반응물 2

HCID 712FormaldehydeHCID 66918942HCID 66918942, 화합물

생성물 1

HCID 66919001HCID 66919001, 화합물

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

N-Cyclopropyl-4-methyl-3-[4-oxo-6-[(2S)-pyrrolidin-2-ylmethoxy]quinazolin-3(4H)-yl]benzamide (0.15 g) and 38% aqueous formaldehyde (0.284 ml) were stirred in formic acid (3 ml) at 90° C. for 16 hours and then concentrated. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution. The organic layer was washed with brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 10% methanol/ethyl acetate followed by 10% methanol/ethyl acetate+1% aqueous ammonia solution to give the title compound (0.12 g) as a white foam solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 1.70 (m, 3H), 1.99 (m, 1H), 2.14 (s, 3H), 2.22 (m, 1H), 2.39 (s, 3H), 2.62 (m, 1H), 2.85 (m, 1H), 2.96 (m, 1H), 3.99 (m, 1H), 4.09 (m, 1H), 7.52 (m, 2H), 7.60 (s, 1H), 7.73 (d, 1H), 7.83 (s, 1H), 7.91 (d, 1H), 8.19 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 433.

후처리

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customPurification by column chromatography on a silica column
  7. washeluting with 10% methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-1ee75d9612234ce29d88d7aed7918117
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750154B2

반응 노트

불러오는 중…