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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Water → 3-(Phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047123
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HRID 1047123 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[N:15][C:16]([NH:28][C:29](=[O:33])[NH:30][CH2:31][CH3:32])=[CH:17][C:18]=3[C:19]3[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=3)=[CH:10][N:11]=2)[C:6](=[O:34])[C:5]([C:35]([O:37][CH2:38][CH2:39][CH2:40][O:41][P:42]([O:52]CC2C=CC=CC=2)([O:44]CC2C=CC=CC=2)=[O:43])=[O:36])=[CH:4]1)[CH3:2].C[Si](Br)(C)C.O>ClCCl.CO>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[N:15][C:16]([NH:28][C:29](=[O:33])[NH:30][CH2:31][CH3:32])=[CH:17][C:18]=3[C:19]3[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=3)=[CH:10][N:11]=2)[C:6](=[O:34])[C:5]([C:35]([O:37][CH2:38][CH2:39][CH2:40][O:41][P:42]([OH:44])([OH:52])=[O:43])=[O:36])=[CH:4]1)[CH3:2]
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참가 물질

6

반응물 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 687463213-{[Bis(benzyloxy)phosphoryl]oxy}propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

생성물 1

HCID 687478433-(Phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate수율 41.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

3-{[Bis(benzyloxy)phosphoryl]oxy}propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 21, 700 mg, 0.82 mM) was dissolved in dry dichloromethane (40 mL), and the reaction mixture was cooled to 0° C. Trimethylsilyl bromide (251 mg, 1.64 mmol) was added and the mixture was stirred for 16 h at room temperature. A solid formed on the walls of round bottom flask. The solvent was decanted and the solid was washed with ethyl acetate (30 mL) to give crude compound. The crude compound was dissolved in methanol (20 mL) and water (30 mL) was added to precipitate the product which was filtered and dried to afford 230 mg (35%) of 3-(phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate.

후처리

  1. customA solid formed on the walls of round bottom flask
  2. customThe solvent was decanted
  3. washthe solid was washed with ethyl acetate (30 mL)
  4. customto give crude compound
  5. customto precipitate the product which
  6. filtrationwas filtered
  7. customdried

출처 및 근거

ORD 기록
ord-5973762b95c949fb848785701b03830b
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569484B2

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