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Triethylamine → N-[2-({2-[3-(4-cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-ethylamino}-methyl)-phenyl]-3-hydroxy-benzamide

HRID 278193
ノート
印刷プレビュー

反応式

HRID 278193 の反応式
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([F:20])[CH:13]=2)[CH:9]=[N:8][CH:7]=1.CCN(CC)CC.[CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:37](=[O:45])[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=1)=O.[BH3-]C#N.[Na+]>CO>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:11][N:10]2[C:6]([CH2:5][CH2:4][NH:3][CH2:28][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=3)=[CH:7][N:8]=[CH:9]2)=[CH:13][C:14]=1[F:20])#[N:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 22627093N-(2-formyl-phenyl)-3-hydroxy-benzamideHCID 226271054-[5-(2-Amino-ethyl)-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride

生成物 1

HCID 22627116N-[2-({2-[3-(4-cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-ethylamino}-methyl)-phenyl]-3-hydroxy-benzamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

To a solution of 4-[5-(2-amino-ethyl)-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride (Step F) (0.64 g, 2.03 mmol) in MeOH (15 mL) was added NEt3 dropwise to pH=4.5. To this solution was added N-(2-formyl-phenyl)-3-hydroxy-benzamide (0.64 g, 2.64 mmol) and NaCNBH3 (0.255 g, 4.06 mmol), and the reaction was stirred 18 h at 25° C. The MeOH was removed in vacuo, and the residue was partitioned with EtOAc and saturated NaHCO3. The organic layer was separated and washed 3× with 10% HCl. The acidic layers were combined, made basic with Na2CO3, then extracted 3× with EtOAc. These layers were combined, washed with brine and dried (MgSO4). Filtration and concentration in vacuo gave the crude product which was purified by prep HPLC to obtain the title compound.

後処理

  1. customThe MeOH was removed in vacuo
  2. customthe residue was partitioned with EtOAc and saturated NaHCO3
  3. customThe organic layer was separated
  4. washwashed 3× with 10% HCl
  5. extractionextracted 3× with EtOAc
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration in vacuo
  9. customgave the crude product which
  10. customwas purified by prep HPLC

出典と根拠

ORDレコード
ord-bc6629a8dce643dcb696410e69f76743
出典データセット
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06358985B1

反応ノート

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