Sodium Hydroxide → N-{4-Methyl-3-[3-methyl-6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)-5-(piperazin-1-yl)benzamide

HRID 1055708노트

반응식

HRID 1055708 반응식
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]4[N:20]([C:21]5[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=5[CH3:28])[NH2:24])[CH:19]=[C:18]([CH3:29])[N:16]4[N:17]=3)[CH:10]=[N:9]2)=CC=1.C(OC([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:46]=[C:47]([CH:51]=[C:52]([S:54]([F:59])([F:58])([F:57])([F:56])[F:55])[CH:53]=2)[C:48](O)=[O:49])[CH2:41][CH2:40]1)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>CN(C=O)C.FC(F)(F)C(O)=O>[CH3:28][C:27]1[CH:26]=[CH:25][C:23]([NH:24][C:48](=[O:49])[C:47]2[CH:46]=[C:45]([N:42]3[CH2:43][CH2:44][NH:39][CH2:40][CH2:41]3)[CH:53]=[C:52]([S:54]([F:59])([F:58])([F:57])([F:55])[F:56])[CH:51]=2)=[CH:22][C:21]=1[N:20]1[C:15]2[N:16]([N:17]=[C:13]([C:11]3[CH:12]=[N:8][NH:9][CH:10]=3)[CH:14]=2)[C:18]([CH3:29])=[CH:19]1

참가 물질

8

반응물 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896995763-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 896998613-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-3-methyl-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylaniline

생성물 1

HCID 136630246N-{4-Methyl-3-[3-methyl-6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)-5-(piperazin-1-yl)benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6422Trifluoroacetic acid용매

실험 절차

65 mg (0.16 mmol) of the compound of Example 9A, 68 mg (0.158 mmol) of the compound of Example 16A and 72 mg (0.19 mmol) of HATU were initially charged in 0.9 ml of DMF, 0.033 ml (0.19 mmol) of N,N-diisopropylethylamine were added and the mixture was stirred at RT for 1 h. The reaction was then stirred into 10 ml of 0.1 M aqueous sodium hydroxide solution. After 10 min of further stirring at RT, the precipitate formed was filtered off, washed with water and dried. The intermediate obtained in this manner was dissolved in 0.5 ml of trifluoroacetic acid and stirred at 80° C. for 6 h. The mixture was then concentrated under reduced pressure and the residue was purified by double preparative HPLC (Method 18). This gave 18 mg (19% of theory) of the title compound.

후처리

  1. stirringAfter 10 min of further stirring at RT
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried
  6. customThe intermediate obtained in this manner
  7. stirringstirred at 80° C. for 6 h
  8. concentrationThe mixture was then concentrated under reduced pressure
  9. customthe residue was purified by double preparative HPLC (Method 18)

출처 및 근거

ORD 기록
ord-a891aa5f101f47ecbf3ffe44aa508010
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394309B2

반응 노트

불러오는 중…