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Morpholine → N-[5-(3-Methoxy-phenyl)-1H-pyrazol-3-yl]-4-morpholin-4-yl-butyramide

HRID 1695217
ノート
印刷プレビュー

反応式

HRID 1695217 の反応式
COC1C=C(C2C=C(N)NN=2)C=CC=1.C(N(C(C)C)CC)(C)C.Br[CH2:25][CH2:26][CH2:27][C:28]([NH:30][C:31]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=2)[NH:33][N:32]=1)=[O:29].[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>CC(N(C)C)=O.C(Cl)Cl>[CH3:43][O:42][C:38]1[CH:37]=[C:36]([C:34]2[NH:33][N:32]=[C:31]([NH:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH:35]=2)[CH:41]=[CH:40][CH:39]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 671875504-bromo-N-[5-(3-methoxy-phenyl)-1H-pyrazol-3-yl]-butyramideHCID 178489814HCID 178489814、化合物

生成物 1

HCID 25029480N-[5-(3-Methoxy-phenyl)-1H-pyrazol-3-yl]-4-morpholin-4-yl-butyramide

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of 4-bromobutyryl chloride chloride (0.104 mL, 0.9 mmol) in dry DMA (1 mL) was cooled to −10° C. (ice/water bath) under N2; 5-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine (170 mg, 0.9 mmol) and diisopropylethylamine (0.315 mL, 1.8 mmol) in dry DMA (1 ml) were added. Upon complete conversion to the intermediate 4-bromo-N-[5-(3-methoxy-phenyl)-1H-pyrazol-3-yl]-butyramide (as monitored by LC-MS), morpholine (0.079 mL, 0.9 mmol) was added and the mixture was heated at 60° C. for 16 hours. The residue was dissolved in DCM (2 mL) and washed with sat. Na2CO3 solution, The organic phase was concentrated under reduced pressure and the crude product was purified by SiO2 column (gradient from Acetonitrile 100% to MeCN/MeOH, NH3 90/10). The fractions containing the title compound were collected to afford 17 mg (5.5% of yield).

後処理

  1. washwashed with sat. Na2CO3 solution
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe crude product was purified by SiO2 column (gradient from Acetonitrile 100% to MeCN/MeOH, NH3 90/10)
  4. additionThe fractions containing the title compound
  5. customwere collected
  6. customto afford
  7. custom17 mg (5.5% of yield)

出典と根拠

ORDレコード
ord-51f93f3ebe0040c5bece6048fd271d5b
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163729B2

反応ノート

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