Morpholine → HCID 59240601、化合物

HRID 42212ノート

反応式

HRID 42212 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 59240601HCID 59240601、化合物収率 80%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-a26ad2e753bb4026a132d7e22ae2c2a0
出典データセット
uspto-grants-2013_09
特許番号
US08536168B2

反応ノート

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