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Hydrochloric Acid → 4-(3-Chloro-phenyl)-2-[6-(4-methyl-piperazine-1-carbonyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide

HRID 1667700
ノート
印刷プレビュー

反応式

HRID 1667700 の反応式
[C:1]([C:4]1[S:8][C:7]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]([OH:20])=O)[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)=[N:6][C:5]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)(=[O:3])[NH2:2].[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)N=N1)C.F[P-](F)(F)(F)(F)F.Cl>O.CN(C)C=O>[Cl:27][C:23]1[CH:22]=[C:21]([C:5]2[N:6]=[C:7]([N:9]3[C:13]4[CH:14]=[C:15]([C:18]([N:32]5[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]5)=[O:20])[CH:16]=[CH:17][C:12]=4[N:11]=[CH:10]3)[S:8][C:4]=2[C:1]([NH2:2])=[O:3])[CH:26]=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 9886HexafluorophosphateHCID 531671-MethylpiperazineHCID 674273413-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acidHCID 178484285HCID 178484285、化合物

生成物 1

HCID 46830580
4-(3-Chloro-phenyl)-2-[6-(4-methyl-piperazine-1-carbonyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 0.05 g (0.15 mmole) of 3-[5-Carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (I.10a), 0.050 mL of N-methyl-piperazine, 0.070 g (0.18 mmole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium, 3-oxide, hexafluorophosphate(1-) (1:1) and 4 mL of dimethylformamide was stirred at room temperature for 16 hours. The mixture was poured into 50 mL of water and made acidic by addition of 1 M hydrochloric acid. The aqueous layer was extracted three times with 20 mL of ethyl acetate and then made basic by addition of potassium carbonate solution. The mixture was extracted three times with 20 ml, of ethyl acetate. The combined organic extracts were washed with 20 mL of water, 20 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (7:93) to give 0.021 g of 4-(3-chloro-phenyl)-2-[6-(4-methyl-piperazine-1-carbonyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.11) as a yellow solid. MH+/Z=481

後処理

  1. extractionThe aqueous layer was extracted three times with 20 mL of ethyl acetate
  2. additionmade basic by addition of potassium carbonate solution
  3. extractionThe mixture was extracted three times with 20 ml
  4. washThe combined organic extracts were washed with 20 mL of water, 20 mL of brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with methanol-dichloromethane (7:93)

出典と根拠

ORDレコード
ord-f9517a37b16c402ba733dab8309abf22
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044213B2

反応ノート

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