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

HRID 1667699Notes

Reaction equation

HRID 1667699 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-685e7e24d4d64b43ac9f54549bb44efd
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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