Dicyclohexylcarbodiimide → HCID 71515463、化合物

HRID 1855213ノート

反応式

HRID 1855213 の反応式
[Cl:1][CH2:2][CH2:3][N:4]([CH2:15][CH2:16][Cl:17])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:33]([C:37]1[O:41][C:40]([CH2:42][S:43][C:44]2[S:48][C:47]([NH2:49])=[N:46][CH:45]=2)=[N:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:17][CH2:16][CH2:15][N:4]([CH2:3][CH2:2][Cl:1])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:49][C:47]2[S:48][C:44]([S:43][CH2:42][C:40]3[O:41][C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:38][N:39]=3)=[CH:45][N:46]=2)=[O:14])=[CH:9][CH:10]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 25306PhenacidHCID 110654845-(((5-(tert-Butyl)oxazol-2-yl)methyl)thio)thiazol-2-amine

生成物 1

HCID 71515463HCID 71515463、化合物収率 76%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred methylene chloride solution (20 ml) was added DMAP (438 mg, 3.59 mmol) and 2-(4-(bis(2-chloroethyl)amino)phenyl)acetic acid (B-5) (906 mg, 3.27 mmol). Subsequently, DCC (690 mg, 3.35 mmol) was added to reaction mixture, followed by addition of 5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-amine (Intermediate CY-200) (800 mg, 2.97 mmol). The mixture was stirred at r.t for 24 h. After removing dicyclohexylurea (DCU) by filtration, the filtrate was concentrated in vacuum and dried over Na2SO4. The residue was purified by silica gel chromatography eluting with CH2Cl2: EtOAc=20:1 to afford total product (1.2 g, 76%) as a gray solid. LC-MS: (M+H)+=528. 1H NMR (300 MHz, CDCl3) δ 10.17 (s, 1H), 7.28-7.30 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.69 (d, J=8.7 Hz, 2H), 6.58 (s, 1H), 3.95 (s, 2H), 363-3.79 (m, 10H), 1.26 (s, 9H).

後処理

  1. customAfter removing dicyclohexylurea (DCU)
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuum
  4. dry with materialdried over Na2SO4
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-d7b30cf313d545548dbd3ad41ef646d1
出典データセット
uspto-grants-2015_02
特許番号
US08962855B2

反応ノート

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