Triethylamine → HCID 178511967、化合物

HRID 423961

反応式

HRID 423961 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1F)[C:6]([NH:8][C@H:9]([C:17]1[NH:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[N:21]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])#[N:2].C(C1C=C(C=CC=1F)C(O)=O)#N.C([N:48](CC)CC)C.F[P-](F)(F)(F)(F)F.[N:60]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=[N:61]1>C1COCC1.O>[NH2:2][C:1]1[C:3]2[C:32](=[CH:31][CH:30]=[C:5]([C:6]([NH:8][C@H:9]([C:17]3[NH:18][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([C:28](=[NH:48])[NH2:29])=[CH:24][CH:23]=4)[N:21]=3)[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:7])[CH:4]=2)[NH:61][N:60]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27739323-Cyano-4-fluorobenzoic acidHCID 178509599HCID 178509599、化合物

生成物 1

HCID 178511967HCID 178511967、化合物収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Part B: 3-Cyano-N-{(S)-1-[4-(4-cyano-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-4-fluoro-benzamide: A mixture of the compound of Example 176 Part A (100 mg, 0.28 mmol), 3-cyano-4-fluorobenzoic acid (46 mg, 0.28 mmol), triethylamine (0.085 mL, 0.61 mmol) and BOP (0.18 g, 0.4 mmol) in THF (5 mL) was stirred at rt overnight under N2. Reaction mixture was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with sat'd. NaHCO3 and brine and then dried over anhydrous Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/EtOAc) provided the amide product (88 mg, 72%). 1H NMR (500 MHz, CDCl3) δ 3.41 (dd, J=13.75, 7.15 Hz, 1H) 3.58 (dd, J=13.47, 7.97 Hz, 1H) 5.33 (q, J=7.70 Hz, 1H) 7.01-7.09 (m, 1H) 7.18-7.37 (m, 7H) 7.66 (d, J=8.25 Hz, 2H) 7.85 (d, J=8.25 Hz, 2H) 7.89-7.96 (m, 1H) 7.95-8.03 (m, 1H) 9.74 (s, 1H). m/z 436.1 (M+H)+.

後処理

  1. customReaction mixture
  2. extractionextracted 3× with EtOAc
  3. washThe combined extracts were washed with sat'd
  4. dry with materialNaHCO3 and brine and then dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-9ae21b6241614fcda10b79be34a8ffab
出典データセット
uspto-grants-2012_01
特許番号
US08101778B2

関連ノート

読み込み中…