Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide

HRID 1177552ノート

反応式

HRID 1177552 の反応式
CN([C:4]([O:8][N:9]1N=NC2C=CC=C[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.CNOC.[O:39]1[CH2:44][CH2:43][CH2:42][O:41][CH:40]1[C:45]1[CH:50]=[CH:49][C:48]([C:51]2[S:52][C:53]3[CH:59]=[C:58]([C:60]([OH:62])=O)[CH:57]=[CH:56][C:54]=3[N:55]=2)=[C:47]([F:63])[CH:46]=1>CN(C=O)C.O>[O:39]1[CH2:44][CH2:43][CH2:42][O:41][CH:40]1[C:45]1[CH:50]=[CH:49][C:48]([C:51]2[S:52][C:53]3[CH:59]=[C:58]([C:60]([N:9]([O:8][CH3:4])[CH3:10])=[O:62])[CH:57]=[CH:56][C:54]=3[N:55]=2)=[C:47]([F:63])[CH:46]=1

参加物

7

反応物 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 671115482-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid

生成物 1

HCID 866387232-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

HBTU (0.80 g, 2.11 mmol) was added to a solution of di-isopropylethylamine (0.61 mL, 3.52 mmol), N,O-dimethylhydroxylamine hydrochloride (0.21 g, 2.11 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid (0.51 g, 1.41 mmol) in DMF (7 mL). The reaction mixture was stirred for 30 min, diluted with water, and extracted with EtOAc three times. The combined extracts were dried (MgSO4), concentrated under vacuum, and purified by silica gel chromatography to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide as an oil. MS (ESI) m/z: Calculated: 402.1; Observed: 403.1 (M++1).

後処理

  1. extractionextracted with EtOAc three times
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-357d324dff4a4893838a36d48bbbc423
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

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