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

HRID 1177552노트

반응식

HRID 1177552 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-357d324dff4a4893838a36d48bbbc423
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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