Methylamine → HCID 68630541、化合物

HRID 2037366ノート

反応式

HRID 2037366 の反応式
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:16][N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[CH2:26][CH2:27][C:28](O)=[O:29])[CH3:2].C[CH2:32][N:33](C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN>CN(C=O)C.C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:16][N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[CH2:26][CH2:27][C:28]([NH:33][CH3:32])=[O:29])[CH3:2]

参加物

8

反応物 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 68629896HCID 68629896、化合物

生成物 1

HCID 68630541HCID 68630541、化合物収率 93.5%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid (40 mg 89 μmol) in DMF (5 mL), DIPEA (35 mg, 268 μmol) is added. The mixture is cooled to 0° C. before PyBOP (51 mg, 98 μmol) is added. The mixture is stirred at 0° C. for 15 min before methylamine (58 μL of a 2 M solution in THF) is added. The mixture is stirred at rt for 16 h, diluted with sat. aq. NaHCO3 solution, and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates using heptane:EA 1:4 to give the title compound (35 mg) as a white solid; LC-MS: tR=1.10 min, [M+H]+=421.25; 1H NMR (CDCl3): δ 1.00 (d, J=6.5 Hz, 6H), 1.31 (t, J=7.3 Hz, 3H), 1.89-2.00 (m, 1H), 2.34-2.41 (m, 2H), 2.44 (s, 3H), 2.47 (s, 3H), 2.63 (d, J=7.0 Hz, 2H), 2.76 (q, J=7.8 Hz, 2H), 2.85 (d, J=4.5 Hz, 3H), 3.06-3.13 (m, 2H), 5.38 (s br, 1H), 7.91 (s, 1H), 7.93 (s, 1H), 8.10 (s, 1H), 8.55 (s, 1H).

後処理

  1. additionis added
  2. additionis added
  3. extractionextracted twice with EA
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified on prep

出典と根拠

ORDレコード
ord-b3785d140a8045d492ad0ca1004229f1
出典データセット
uspto-grants-2013_11
特許番号
US08575200B2

反応ノート

読み込み中…