Diisopropylethylamine → HCID 178522958, 화합물

HRID 1875051노트

반응식

HRID 1875051 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[C:28]([F:34])[C:27]=1[O:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1.[Cl:46][C:47]1[N:48]=[C:49]([CH:55]2[CH2:57][CH2:56]2)[NH:50][C:51]=1[C:52](O)=[O:53].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:46][C:47]1[N:48]=[C:49]([CH:55]2[CH2:56][CH2:57]2)[NH:50][C:51]=1[C:52]([NH:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([Cl:25])=[C:27]([O:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=[CH:38][CH:37]=2)[C:28]=1[F:34])=[O:53]

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 68486009{[4-Chloro-2-fluoro-3-(1-naphthalenyloxy)phenyl]methyl}amineHCID 178524911HCID 178524911, 화합물

생성물 1

HCID 178522958HCID 178522958, 화합물수율 17.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (0.113 g, 0.298 mmol) was added to a solution of {[4-chloro-2-fluoro-3-(1-naphthalenyloxy)phenyl]methyl}amine (0.060 g, 0.199 mmol) and 4-chloro-2-cyclopropyl-1H-imidazole-5-carboxylic acid (0.037 g, 0.199 mmol) and diisopropylethylamine (0.052 mL, 0.298 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 1 hr. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA) to give the title compound (0.016 g, 14%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.284-8.37 (m, 1H), 8.00-8.13 (m, 1H), 7.95 (dd, 1H), 7.54-7.66 (m, 3H), 7.48 (dd, 1H), 7.25-7.37 (m, 2H), 6.49 (d, 1H), 4.33-4.62 (d, 2H), 1.75-2.03 (m, 1H), 0.85-0.93 (m, 2H), 0.77-0.84 (m, 2H). ES MS: m/z 470 (M+1).

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA)

출처 및 근거

ORD 기록
ord-2ee320fde7c44952a4947e59538fb6c8
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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