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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sodium Bicarbonate → 1-(2-{4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide Hydrochloride

HRID 657084
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HRID 657084 반응식
[ClH:1].Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[CH:20]=[C:19]([F:22])[CH:18]=[N+:17]([O-:23])[C:16]=3[CH:15]=[CH:14][C:13]2=[O:24])[CH2:6][CH2:5]1.[O:25]1[C:30]2=[CH:31][N:32]=[C:33]([CH:35]=O)[CH:34]=[C:29]2C[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=[O:39])C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.C(N(CC)CC)C.CO>[ClH:1].[O:39]1[C:29]2[CH:34]=[C:33]([CH2:35][NH:3][CH:4]3[CH2:5][CH2:6][N:7]([CH2:10][CH2:11][N:12]4[C:21]5[CH:20]=[C:19]([F:22])[CH:18]=[N+:17]([O-:23])[C:16]=5[CH:15]=[CH:14][C:13]4=[O:24])[CH2:8][CH2:9]3)[N:32]=[CH:31][C:30]=2[O:25][CH2:26][CH2:27]1
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참가 물질

9

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 566403113,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehydeHCID 688201601-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide Dihydrochloride

생성물 1

HCID 689927451-(2-{4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide Hydrochloride

시약·촉매·용매 4

HCID 887Methanol용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

1-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide dihydrochloride (100 mg, 0.264 mmol) was stirred in chloroform (2 mL) plus methanol (0.1 mL), and triethylamine (0.130 mL) was added. After stirring for 10 minutes at room temperature 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 126(e)) (44 mg, 1 eq.) was added and the mixture was stirred at rt for a further 3 hours before addition of sodium triacetoxyborohydride (168 mg, 3 eq.). After a further 3 hours, saturated aqueous sodium hydrogen cabonate (1 ml) was added and the organic phase was diluted with DCM to bring the total volume to ca. 50 ml. The organic phase was separated using a hydrophobic frit and the aqueous phase was extracted with DCM (2×20 ml). The combined DCM extracts were evaporated under reduced pressure and purified by MDAP to give the free base of the title compound as a tan amorphous solid (39 mg).

후처리

  1. additionwas added
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with DCM (2×20 ml)
  4. customThe combined DCM extracts were evaporated under reduced pressure
  5. custompurified by MDAP

출처 및 근거

ORD 기록
ord-02bd0a6f09ba4d6a88e72219a0979411
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071592B2

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