1,2-Dichloroethane → HCID 178445681、化合物

HRID 1992804ノート

反応式

HRID 1992804 の反応式
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][N:21]=3)[N:17]=[C:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.[NH2:47][C:48]1[NH:52][N:51]=[N:50][N:49]=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:47][C:48]4[NH:52][N:51]=[N:50][N:49]=4)=[O:26])=[CH:22][N:21]=3)[N:17]=[C:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 178445683HCID 178445683、化合物HCID 178509299HCID 178509299、化合物

生成物 1

HCID 178445681HCID 178445681、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of the intermediate from example 8 step H (65 mg, 0.122 mmol) in DMF (2 mL) was added HOAt (25 mg, 0.184 mmol), amino tetrazole(32 mg, 0.36 mmol), DIEA (64 μL, 0.37 mmol) and EDC (36 mg, 0.184 mmol). The reaction was stirred at 50° C. for 18 hours. The reaction was diluted with ethyl acetate and washed with 1N HCl and saturated NaCl solution. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified on the Gilson reverse phase HPLC to give the title compound. 1H NMR (DMSO, 500 MHz): 9.12 (s, 1H), 8.4 (dd, J=2.0, 9.1 Hz, 2H), 8.18 (d, J=6.6 Hz, 1H), 8.03 (d, J=1.9 Hz, 1H), 7.83 (dd, J=1.9, 8.3 Hz, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.53 (s, 1H), 7.24 (d, J=8.2 Hz, 1H), 7.24 (d, J=8.2 Hz, 1H), 5.91 (s, 2H), 3.96 (bm, 1H), 1.83 (d, J=12.3 Hz, 2H), 1.48 (m, 3H), 1.28 (m, 2H), 0.98 (m, 1H), 0.82 (s, 9H). LC-MS=2.71 min; (M+H)=596.2.

後処理

  1. washwashed with 1N HCl and saturated NaCl solution
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on the Gilson reverse phase HPLC

出典と根拠

ORDレコード
ord-c48423cc519c4064827e18c79e77baac
出典データセット
uspto-grants-2010_01
特許番号
US07649009B2

反応ノート

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