Triethylamine → HCID 24989980, compound

HRID 659145Notes

Reaction equation

HRID 659145 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.[Cl-].[NH4+].[B-](F)(F)(F)F.CCOC(C(C#N)=[N:33]OC(N(C)C)=[N+](C)C)=O.C(N(CC)CC)C>CN(C=O)C>[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]([NH2:33])=[O:19])[S:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 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 24989980HCID 24989980, compoundYield 28.3%

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), ammonium chloride (19.4 mg, 0.36 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 14 mg (28%) of the desired product. MS: M+H+=276.03.

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-3f9a4cb23f5a41b289b0122f7fb3ce35
Source dataset
uspto-grants-2011_12
Patent number
US08080569B2

Reaction notes

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