Diisopropylethylamine → HCID 86296367、化合物

HRID 930827ノート

反応式

HRID 930827 の反応式
[F:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:45]=[CH:46][C:47]([Cl:66])=[C:48]([C:50]2[N:51]=[C:52]3[N:57]=[CH:56][C:55]([NH:58][C:59](=[O:64])[O:60][CH:61]([CH3:63])[CH3:62])=[CH:54][N:53]3[CH:65]=2)[CH:49]=1>CN(C=O)C>[Cl:66][C:47]1[CH:46]=[CH:45][C:44]([NH:43][C:7]([C:5]2[O:6][C:2]([F:1])=[CH:3][CH:4]=2)=[O:9])=[CH:49][C:48]=1[C:50]1[N:51]=[C:52]2[N:57]=[CH:56][C:55]([NH:58][C:59](=[O:64])[O:60][CH:61]([CH3:62])[CH3:63])=[CH:54][N:53]2[CH:65]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 213638875-Fluoro-2-furancarboxylic acidHCID 90444845HCID 90444845、化合物

生成物 1

HCID 86296367HCID 86296367、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a 40 mL vial isopropyl (2-(5-amino-2-chlorophenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (I-9) (30 mg, 0.09 mmol) was dissolved in DMF (Volume: 0.3 mL). 5-fluorofuran-2-carboxylic acid (11 mg, 0.09 mmol) was then added to the reaction mixture followed by HATU (65.98 mg, 0.17 mmol) and (iPr)2NEt (0.043 mL, 0.26 mmol). The reaction was stirred at rt for 8 hrs. The reaction was monitored was LCMS which indicated the reaction was complete with a new peak of desired mass was observed (M+H=468.1). The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mL). Combined all organics, dried over sodium sulfate and concentrated under reduce pressure. The crude reaction purified by reverse phase HPLC yeild 2-(2-chloro-5-(5-fluorofuran-2-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (1). The TFA salt was neutralized to a free base by a HCO3 column. 1H NMR (400 MHz, DMSO) δ 10.41 (s, 1H), 10.01 (s, 1H), 9.31 (s, 1H), 8.69 (s, 1H), 8.61 (d, J=2.7, 1H), 8.51 (d, J=2.7, 1H), 7.87 (dd, J=2.7, 8.8, 1H), 7.53 (d, J=8.7, 1H), 7.47 (t, J=3.6, 1H), 6.11 (dd, J=3.7, 7.1, 1H), 5.03-4.85 (m, 1H), 1.29 (d, J=6.2, 6H). M/Z=(458.1M+1). RT=1.64 min.

後処理

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude reaction
  6. custompurified by reverse phase HPLC yeild 2-(2-chloro-5-(5-fluorofuran-2-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (1)

出典と根拠

ORDレコード
ord-692ffe6ee91d44f48e5bfb31dc6331b7
出典データセット
uspto-grants-2016_03
特許番号
US09296754B2

反応ノート

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