Triethylamine → HCID 178511967, 화합물

HRID 1020921노트

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HRID 1020921 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 178511967HCID 178511967, 화합물수율 72%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ba0fb6468f544d59b8f3705cd3c4a8fa
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716492B2

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