N-Methylaniline → HCID 16029632, compound

HRID 659143Notes

Reaction equation

HRID 659143 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[C:13]([CH3:16])=[C:12]([C:17]([OH:19])=O)[S:11]3)=[CH:4][CH:3]=1.[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(CC)CC)C>CN(C=O)C>[CH3:20][N:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17]([C:12]1[S:11][C:10]2=[N:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:15][N:14]2[C:13]=1[CH3:16])=[O:19]

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226936536-(4-Fluorophenyl)-3-methylimidazo[2,1-b][1,3]thiazole-2-carboxylic acid

Product 1

HCID 16029632HCID 16029632, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(4-Fluoro-phenyl)-3-methyl-imidazo[2,1-b]thiazole-2-carboxylic acid (example 7, 50 mg, 0.18 mmol) N-methyl-phenyl-amine (29.15 mg, 0.27 mmol), TOTU (63.32 mg, 0.2 mmol) and triethylamine (100.6 μl, 0.72 mmol) in 3 ml DMF were stirred at RT for 8 hours. The mixture was evaporated. Ethyl acetate and water were added, the organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 9 mg (14%) of the desired product. MS: M+H+=365.94.

Workup

  1. customThe mixture was evaporated
  2. additionEthyl acetate and water were added
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-1699bd428a60451484294fe5ddd82f25
Source dataset
uspto-grants-2011_12
Patent number
US08080569B2

Reaction notes

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