Diisopropylethylamine → 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

HRID 575045ノート

反応式

HRID 575045 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:17][CH:10]([CH2:11]1)[N:9]1[C:5]2=[N:6][C:7]([C:18]([OH:20])=O)=[CH:8]1.C[N:22](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N.O>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:17][CH:10]([CH2:11]1)[N:9]1[C:5]2=[N:6][C:7]([C:18]([NH2:22])=[O:20])=[CH:8]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12896473Azane;hydrateHCID 8669307810-Bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylic acid

生成物 1

HCID 8669308010-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide収率 54%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Into a 5000-mL 4-necked round-bottom flask was placed a solution of 9-bromo-10-fluoro-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxylic acid (280 g, 830.51 mmol, 1.00 equiv) in N,N-dimethylformamide (2500 mL), HBTU (315 g, 830.61 mmol, 1.00 equiv), and DIEA (139 g, 1.08 mol, 1.30 equiv). The resulting solution was stirred at room temperature for 1.5 h. This was followed by the addition of amine hydrate (300 mL). The resulting solution was stirred at room temperature for 0.5 h and diluted with 2000 mL of H2O. The solids were collected by filtration, washed with 3×1000 mL of water and dried to afford 150.6 g (54%) of 9-bromo-10-fluoro-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxamide as a white solid. LC-MS: [M+H]+336 1H-NMR (DMSO, 300 MHz, ppm) □ 1.66-1.70 (2H, m), 3.08-3.12 (2H, m), 3.70-3.71 (1H, m), 4.88-4.94 (1H, m), 7.14 (1H, s), 7.36-7.39 (1H, m), 7.60 (1H, s), 7.83 (1H, s), 8.84-8.86 (1H, m).

後処理

  1. customInto a 5000-mL 4-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred at room temperature for 0.5 h
  3. filtrationThe solids were collected by filtration
  4. washwashed with 3×1000 mL of water
  5. customdried

出典と根拠

ORDレコード
ord-c1a144bf16324123be47e98cf50df8db
出典データセット
uspto-grants-2015_05
特許番号
US09034866B2

反応ノート

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