Morpholine → HCID 59240601, 화합물

HRID 42212노트

반응식

HRID 42212 반응식
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][N:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)=[CH:28][N:29]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 574716176-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridine-3-carbaldehyde

생성물 1

HCID 59240601HCID 59240601, 화합물수율 80%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-[4-(4-benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridine-3-carbaldehyde (40 mg, 0.1 mmol) in 5 mL DCM is added a drop of acetic acid, NaBH(OAc)3 (41.4 mg, 0.2 mmol) and morpholine (7.5 mL, 0.12 mmol). The reaction mixture is stirred for 30 min at rt. Aqueous NaHCO3 solution is added and the reaction mixture is stirred for an additional 30 min. The layers are separated and the aqueous layer is extracted with DCM. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography on silica gel (EtOAc/heptane 10%-70%) to yield the title compound (37.8 mg, 80%).

후처리

  1. stirringthe reaction mixture is stirred for an additional 30 min
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with DCM
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by flash chromatography on silica gel (EtOAc/heptane 10%-70%)

출처 및 근거

ORD 기록
ord-a26ad2e753bb4026a132d7e22ae2c2a0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

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