Sodium Bicarbonate → HCID 68991018, 화합물

HRID 656971노트

반응식

HRID 656971 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[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]=[CH:14][C:13]2=[O:23])[CH2:6][CH2:5]1.O=[C:25]1[CH2:30][O:29][C:28]2[CH:31]=[CH:32][C:33]([CH:35]=O)=[N:34][C:27]=2N1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.C(N(CC)CC)C.C(Cl)(Cl)Cl>[ClH:1].[ClH:1].[O:29]1[C:28]2=[CH:27][N: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[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=5)[N:15]=[CH:14][C:13]4=[O:23])[CH2:8][CH2:9]3)[CH:32]=[C:31]2[CH2:25][CH2:30]1

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 688175421-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride

생성물 1

HCID 68991018HCID 68991018, 화합물수율 91%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 8471Triethylamine용매

실험 절차

A solution of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride (60 mg; 0.166 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003087098, Example 31(e))(35 mg, 0.20 mmol) in MeOH (3 ml), chloroform (3 ml) and triethylamine (0.06 ml) was heated under reflux with 3A molecular sieves overnight. It was cooled and sodium triacetoxyborohydride (0.11 g; 0.52 mmol) was added, and the mixture was stirred at rt for 7-8 h. Aqueous sodium bicarbonate solution was added to basify and the aqueous phase was extracted several times with 10% MeOH-DCM. The organic fractions were dried and evaporated. Chromatography on silica gel, eluting with 0-20% MeOH-DCM gave the free base of the title compound (68 mg, 91%).

후처리

  1. temperatureIt was cooled
  2. extractionthe aqueous phase was extracted several times with 10% MeOH-DCM
  3. customThe organic fractions were dried
  4. customevaporated
  5. washChromatography on silica gel, eluting with 0-20% MeOH-DCM

출처 및 근거

ORD 기록
ord-0b9e9747144e4f8d8f32c4a28f54c613
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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