Triethylamine → N-(4-Chlorobenzyl)4-hydroxy-1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazine-3-carboxamide 2,2-Dioxide

HRID 411217노트

반응식

HRID 411217 반응식
[CH3:1][N:2]1[C:7]2[S:8][C:9]([C:11]#[C:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)=[CH:10][C:6]=2[C:5](=[O:21])[CH2:4][S:3]1(=[O:23])=[O:22].C(N(CC)CC)C.[Cl:31][C:32]1[CH:41]=[CH:40][C:35]([CH2:36][N:37]=[C:38]=[O:39])=[CH:34][CH:33]=1>CS(C)=O.Cl>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:36][NH:37][C:38]([C:4]2[S:3](=[O:22])(=[O:23])[N:2]([CH3:1])[C:7]3[S:8][C:9]([C:11]#[C:12][CH2:13][O:14][CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][O:16]4)=[CH:10][C:6]=3[C:5]=2[OH:21])=[O:39])=[CH:40][CH:41]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 33723791-Chloro-4-(isocyanatomethyl)benzeneHCID 223972121-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide

생성물 1

HCID 69731037N-(4-Chlorobenzyl)4-hydroxy-1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazine-3-carboxamide 2,2-Dioxide수율 31%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a stirring solution of 1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide (Preparation 35, 0.64 g) and triethylamine (0.27 g) in DMSO (15mL) at ambient temperature is added 4-chloro-benzylisocyanate (0.45 g). The resulting red solution is stirred overnight at ambient temperature and diluted with 10% aqueous HCl (20 mL). The aqueous layer is extracted with EtOAc (3×25 ml). The combined organic layers are dried over MgSO4 and concentrated in vacuo. The residue is dissolved in EtOAc (15 mL) and allowed to stand at ambient temperature overnight. The resulting solid is collected by filtration, washed with EtOAc (10 ml) and dried in vacuo at 50° C. to afford 0.29 g (31%) of the title compound as a tan solid. Physical characteristics: 1H NMR (CDCl3) δ 1.58-1.82, 3.49, 3.60, 3.89, 4.50, 4.56, 4.86, 7.30, 7.42, 7.71, 15.62; IR (diffuse reflectance) 3353, 2945, 1615, 1581, 1541, 1493, 1431, 1366, 1345, 1308, 1296, 1276, 1183, 1119, 1031 cm−1; MS (EI) m/z 522 (M+). Anal. Found: C, 53.17; H, 4.49; N, 5.67.

후처리

  1. extractionThe aqueous layer is extracted with EtOAc (3×25 ml)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in EtOAc (15 mL)
  5. waitto stand at ambient temperature overnight
  6. filtrationThe resulting solid is collected by filtration
  7. washwashed with EtOAc (10 ml)
  8. customdried in vacuo at 50° C.

출처 및 근거

ORD 기록
ord-9260289da59b44bd9b1bf1cf3cabe18b
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559145B2

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