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 1055708ノート

反応式

HRID 1055708 の反応式
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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a891aa5f101f47ecbf3ffe44aa508010
出典データセット
uspto-grants-2016_07
特許番号
US09394309B2

反応ノート

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