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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
ノート
印刷プレビュー

反応式

HRID 1715271 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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、化合物

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8089e3103e08468e91154ee14e9f1321
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799814B2

反応ノート

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