Hydroxyamine hydrochloride → (trans)-N-hydroxy-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamide

HRID 1173025

反応式

HRID 1173025 の反応式
CN(C([O:8][N:9]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[N:27]=[C:28]([C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=2)[S:29][C:30]=1[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([C@@H:39]2[CH2:41][C@H:40]2[C:42](O)=[O:43])=[CH:35][CH:34]=1.Cl.NO.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:8][NH:9][C:42]([C@@H:40]1[CH2:41][C@H:39]1[C:36]1[CH:35]=[CH:34][C:33]([NH:32][CH2:31][C:30]2[S:29][C:28]([C:45]3[CH:46]=[CH:47][C:48]([C:51]([F:53])([F:52])[F:54])=[CH:49][CH:50]=3)=[N:27][C:26]=2[CH3:25])=[CH:38][CH:37]=1)=[O:43]

参加物

6

反応物 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11487291(+)-(trans)-2-{4-[({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid

生成物 1

HCID 11465024(trans)-N-hydroxy-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamide収率 48.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

HATU (0.154 g, 0.41 mmol) and (+)-(trans)-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid (III-3c) (0.135 g, 0.31 mmol) in DMF (10 mL) were stirred at RT for 15 min, then hydroxylamine hydrochloride (0.50 g) was added. The solution was stirred at RT for 1 h, then saturated NaHCO3 solution (20 mL) was added. The resulting solid was filtered, washed with water (10 mL) and dissolved in ethyl acetate (50 mL). The organic layer was dried over MgSO4, filtered and concentrated to give the title compound as a white powder (0.067 g, 48%). 1H NMR (400 MHz, DMSO) δ 10.45 (s, 1H), 8.68 (s, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H), 6.82 (d, J=8.5 Hz, 2H), 6.51 (d, J=8.6 Hz, 2H), 6.21 (t, J=5.7 Hz, 1H), 4.38 (d, J=5.9 Hz, 2H), 2.42 (s, 3H), 2.07-2.02 (m, 1H), 1.48-1.43 (m, 1H), 1.21-1.16 (m, 1H), 1.06-1.01 (m, 1H).

後処理

  1. filtrationThe resulting solid was filtered
  2. washwashed with water (10 mL)
  3. dissolutiondissolved in ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6f87b07cbd96453f97a873c867f2501f
出典データセット
uspto-grants-2010_11
特許番号
US07834013B2

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