1,2-Dichloroethane → 5-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid {1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-yl}-amide

HRID 2065003ノート

反応式

HRID 2065003 の反応式
N#N.[C:3]([Si:7]([CH3:26])([CH3:25])[O:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[O:21][CH:20]=[N:19][C:18]=2[C:22](O)=[O:23])[CH:14]=[CH:15][CH:16]=1)([CH3:6])([CH3:5])[CH3:4].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[CH3:50][C:51]1([C:56]2[O:60][C:59]([CH2:61][N:62]3[CH:66]=[CH:65][C:64]([NH2:67])=[N:63]3)=[CH:58][CH:57]=2)[O:55][CH2:54][CH2:53][O:52]1>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[CH3:50][C:51]1([C:56]2[O:60][C:59]([CH2:61][N:62]3[CH:66]=[CH:65][C:64]([NH:67][C:22]([C:18]4[N:19]=[CH:20][O:21][C:17]=4[C:13]4[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][O:8][Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:26])[CH3:25])[CH:12]=4)=[O:23])=[N:63]3)=[CH:58][CH:57]=2)[O:55][CH2:54][CH2:53][O:52]1

参加物

10

反応物 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669287811-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-ylamineHCID 669288865-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid

生成物 1

HCID 669291035-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid {1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-yl}-amide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-{3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid (130 mg, 0.37 mmol) in CH2Cl2 (2.7 mL) was treated sequentially with DMAP (11 mg, 0.09 mmol), HOBt (60 mg, 0.45 mmol), EDC (179 mg, 0.94 mmol) and DIPEA (0.25 mL, 1.50 mmol) and the reaction mixture was stirred at rt for 1 h. A solution of 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-ylamine (93 mg, 0.37 mmol) in CH2Cl2 (1.0 mL) was then added and the reaction mixture was stirred at rt for 48 h. CH2Cl2 (10 mL) was added followed by water (10 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (1:2 hept-EA) gave the title compound as a colorless oil. TLC: rf (1:2 hept-EA)=0.26. LC-MS-conditions 02: tR=1.22 min, [M+H]+=579.74.

後処理

  1. stirringthe reaction mixture was stirred at rt for 48 h
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residue by FC (1:2 hept-EA)

出典と根拠

ORDレコード
ord-f85ae924f7f8497290962564ccba97e7
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

反応ノート

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