Triethylamine → HCID 57982559, compound

HRID 1868448Notes

Reaction equation

HRID 1868448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])[N:16]=[C:12]3[NH:11][C:10]([CH3:25])=[C:9]2[C:26]([NH2:28])=O)=[CH:4][C:3]=1[F:29].CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])[N:16]=[C:12]3[NH:11][C:10]([CH3:25])=[C:9]2[C:26]#[N:28])=[CH:4][C:3]=1[F:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 57982520HCID 57982520, compound

Product 1

HCID 57982559HCID 57982559, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-(4-chloro-3-fluorophenyl)-2-(2-methoxyphenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-6-carboxamide (351 mg, 0.85 mmol) in CH2Cl2 (10 mL) at 0° C. was added Et3N (0.73 mL, 5.27 mmol) followed by trifluoroacetic anhydride (0.38 mL, 2.72 mmol) over a period of 10 min. The reaction mixture was stirred at 0° C. for an additional 40 min and quenched with 10% Na2CO3 (5 mL) and H2O (10 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was triturated with ether and purified by column chromatography on silica gel eluting from 30% to 50% EtOAc in hexanes to give 5-(4-chloro-3-fluorophenyl)-2-(2-methoxyphenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile (120 mg, 36%) as a yellow solid.

Workup

  1. customquenched with 10% Na2CO3 (5 mL) and H2O (10 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with ether
  8. custompurified by column chromatography on silica gel eluting from 30% to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-5e5d4330c9d4433eafc1018c4b1a0b3a
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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