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Triethylamine → 2'-(acetylamino)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)-4'-methyl-4,5'-bi-1,3-thiazole-2 carboxamide

HRID 1715271
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HRID 1715271 반응식
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](Cl)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[C:28](=[O:29])[O:27][C:26]([CH3:31])([CH3:30])[O:25][C:24]=2[CH:32]=1.C(CC1SC=C(C2SC(NC(=O)C)=NC=2C)N=1)#N.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([NH:19][C:20]3[CH:21]=[CH:22][C:23]4[C:28](=[O:29])[O:27][C:26]([CH3:30])([CH3:31])[O:25][C:24]=4[CH:32]=3)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11989522N-[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]acetamideHCID 231100727-Amino-2,2-dimethyl-4H-1,3-benzodioxine-4-oneHCID 86621993HCID 86621993, 화합물

생성물 1

HCID 866219952'-(acetylamino)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)-4'-methyl-4,5'-bi-1,3-thiazole-2 carboxamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above, (200 mg, 0.66 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 7-Amino-2,2-dimethyl-4H-1,3-benzodioxine-4-one, Amine 3 prepared as described above, (128.0 mg; 0.66 mmol; 1 eq.) and triethylamine (0.19 ml; 1.33 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is purified by crystallization in MeOH. The resulting product is washed with MeOH and NaHCO3 (sat), affording 2′-(acetylamino)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)-4′-methyl-4,5′-bi-1,3-thiazole-2 carboxamide as a beige solid (200 mg; 65%). 1H NMR (DMSO-d6, 300 MHz) δ 1.67 (s, 6H), 2.13 (s, 3H), 2.49 (s, 3H), 7.28 (m, 1H), 7.56 (s, 1H), 7.64 (br d, J=9 Hz, 1H), 7.75 (s, 1H), 11.65 (br s, 1H). M− (ESI): 457.08; M+ (ESI): 459.13. HPLC (method A), Rt: 3.86 min (purity: 97.7%).

후처리

  1. customSolvents are evaporated
  2. customthe crude product is purified by crystallization in MeOH
  3. washThe resulting product is washed with MeOH and NaHCO3 (sat)

출처 및 근거

ORD 기록
ord-8089e3103e08468e91154ee14e9f1321
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07799814B2

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