Triethylamine → [1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl-methyl]-carbamic acid tert-butyl ester

HRID 2270238노트

반응식

HRID 2270238 반응식
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14](Cl)=[C:15]([F:20])[CH:16]=2)[N:11]([CH:22]2[CH2:24][CH2:23]2)[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:30][C:31](=[O:39])[N:32](C1CCNC1)[CH3:33])([CH3:29])([CH3:28])[CH3:27].C([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C>CN(C=O)C.O>[C:26]([O:30][C:31](=[O:39])[NH:32][CH2:33][CH:46]1[CH2:44][CH2:43][N:42]([C:14]2[CH:13]=[C:12]3[C:17]([C:18](=[O:19])[N:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:10](=[O:25])[N:11]3[CH:22]3[CH2:24][CH2:23]3)=[CH:16][C:15]=2[F:20])[CH2:45]1)([CH3:29])([CH3:28])[CH3:27]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidineHCID 226328893-Benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione

생성물 1

HCID 53711025[1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl-methyl]-carbamic acid tert-butyl ester수율 55%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A solution of 3-benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione (Example E-3, 0.162 g, 0.44 mmol) in DMF (3.0 mL) was reacted with pyrrolidin-3-yl-methyl-carbamic acid tert-butyl ester (0.40 g, 2.0 mmol) and triethylamine (0.63 mL, 4.5 mmol) then heated to 70° C. for 2 days. The mixture was then cooled, diluted with H2O, and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 0.127 g of the title compound as a solid.

후처리

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-426de909d1e946aeaca48a76017958fc
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06331538B1

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