2-Aminothiazole → HCID 23114560, compound

HRID 2080432Notes

Reaction equation

HRID 2080432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:19]([F:20])=[CH:18][C:14]([C:15]([OH:17])=O)=[C:13]([CH2:21][C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[N:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S:30]1[CH:34]=[CH:33][N:32]=[C:31]1[NH2:35].N1(O)C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>CCCCCC.C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:19]([F:20])=[CH:18][C:14]([C:15]([NH:35][C:31]3[S:30][CH:34]=[CH:33][N:32]=3)=[O:17])=[C:13]([CH2:21][C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[N:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 21552-AminothiazoleHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23114824HCID 23114824, compound

Product 1

HCID 23114560HCID 23114560, compoundYield 60.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane (2 ml) solution were added 6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoronicotinic acid (100 mg, 0.23 mmol) were added thiazol-2-ylamine (25 mg, 0.25 mmol), benzotriazol-1-ol (34 mg, 0.25 mmol), 4-methylmorpholine (0.027 ml, 0.25 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (48 mg, 0.25 mmol) at room temperature. The resulting mixture was stirred at room temperature for 14 hours. To the reaction mixture was added ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure. The residue was washed with ethanol and collected by filtration to give the title compound (72 mg, 0.14 mmol, 60%) as a white solid.

Workup

  1. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure
  7. washThe residue was washed with ethanol
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c128a817b9b54cceb841d0ec009a7dd8
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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