1,2-Dichloroethane → n-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]-1-methyl-1h-imidazole-5-carboxamide

HRID 885968ノート

反応式

HRID 885968 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:14](=[O:22])[NH:15][C:16]([CH3:21])([CH3:20])[CH2:17][C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[CH3:24][N:25]1[C:29]([C:30](O)=[O:31])=[CH:28][N:27]=[CH:26]1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:20][C:16]1([CH3:21])[NH:15][C:14](=[O:22])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([NH:1][C:30]([C:29]5[N:25]([CH3:24])[CH:26]=[N:27][CH:28]=5)=[O:31])[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27735071-methyl-1H-imidazole-5-carboxylic acidHCID 584416902-(6-amino-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,7-dihydro-6,6-dimethylthiazolo[5,4-c]pyridin-4(5H)-one

生成物 1

HCID 67187232n-[4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]-1-methyl-1h-imidazole-5-carboxamide収率 29%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of Example 42 (0.025 g, 0.08 mmol) in DCM (1 mL) were added 1-methylimidazol-5-ylcarboxylic acid (0.013 g, 0.10 mmol), DIPEA (0.02 mL, 0.10 mmol), EDC (0.030 g, 0.16 mmol) and HOBT (0.05 g, 0.04 mmol). The reaction mixture was stirred at r.t. for 18 h, then concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.01 g, 29%) as a yellow oil. δH (CDCl3) 9.25 (1H, s), 8.46-8.43 (1H, m), 7.33 (1H, dd, J 8.9 and 2.4 Hz), 7.07 (1H, d, J 0.9 Hz), 7.02 (1H, d, J 0.8 Hz), 6.94 (1H, d, J 8.9 Hz), 5.56 (1H, br. s), 4.36-4.29 (2H, m), 4.16-4.09 (2H, m), 4.11 (3H, s), 2.90 (2H, s), 1.40 (6H, s). LCMS (ES+) 439.4 (M+H)+, RT 2.69 minutes (Method 1).

後処理

  1. concentrationconcentrated in vacuo
  2. customPurification by preparative HPLC (Method 6)

出典と根拠

ORDレコード
ord-872b64c81ce3465588ca83f5897b9224
出典データセット
uspto-grants-2012_08
特許番号
US08242116B2

反応ノート

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