Hexafluorophosphate → 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide

HRID 1667699노트

반응식

HRID 1667699 반응식
[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].[NH2:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[CH3:35]N(C(N(C)C)=[N+]1C2C(=NC=CC=2)N=N1)C.F[P-](F)(F)(F)(F)F>O.CN(C)C=O>[CH3:35][N:32]1[CH2:33][CH2:34][CH:29]([NH:28][C:18]([C:15]2[CH:16]=[CH:17][C:12]3[N:11]=[CH:10][N:9]([C:7]4[S:8][C:4]([C:1](=[O:3])[NH2:2])=[C:5]([C:21]5[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=5)[N:6]=4)[C:13]=3[CH:14]=2)=[O:20])[CH2:30][CH2:31]1

참가 물질

7

반응물 4

HCID 9886HexafluorophosphateHCID 4243614-PiperidinamineHCID 674273413-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acidHCID 178484285HCID 178484285, 화합물

생성물 1

HCID 468305793-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.060 g (0.15 mmole) of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (I.10a), 0.06 mL of 4-aminopiperidine, 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 extracted three times with 25 mL of ethyl acetate. The combined organic extracts were washed three times with 20 mL of 1 M hydrochloric acid. The combined aqueous extracts were made basic with potassium carbonate, and the resulting solid collected by filtration, washed with water, and air-dried to give 0.038 g of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide (I.10) as a light yellow solid. MH+/Z=495

후처리

  1. extractionextracted three times with 25 mL of ethyl acetate
  2. washThe combined organic extracts were washed three times with 20 mL of 1 M hydrochloric acid
  3. filtrationthe resulting solid collected by filtration
  4. washwashed with water
  5. customair-dried

출처 및 근거

ORD 기록
ord-685e7e24d4d64b43ac9f54549bb44efd
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044213B2

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