Diisopropylethylamine → HCID 86296367, 화합물

HRID 930827노트

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HRID 930827 반응식
[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

참가 물질

6

반응물 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, 화합물

생성물 1

HCID 86296367HCID 86296367, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-692ffe6ee91d44f48e5bfb31dc6331b7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296754B2

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