Trifluoroacetic anhydride → HCID 46701211, compound

HRID 1799051Notes

Reaction equation

HRID 1799051 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:15]=[CH:16]/[C:17]2[N:21]([C:22]3[N:27]=[N:26][C:25]([C:28]([NH2:30])=O)=[CH:24][CH:23]=3)[C:20]3[CH:31]=[CH:32][CH:33]=[CH:34][C:19]=3[N:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:15]=[CH:16]/[C:17]2[N:21]([C:22]3[N:27]=[N:26][C:25]([C:28]#[N:30])=[CH:24][CH:23]=3)[C:20]3[CH:31]=[CH:32][CH:33]=[CH:34][C:19]=3[N:18]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 67427904HCID 67427904, compound

Product 1

HCID 46701211HCID 46701211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The final compound was prepared by adding triethylamne (80.0 mg, 0.78 mmol) to a stirred solution of Step 2 product (121 mg, 0.263 mmol) dissolved in dry DCM (5 ml) follwed by addition of triflouroacetic anhydride (84 mg, 0.395 mmol) at 0° C., under nitrogen atmosphere and the reaction mixture stirred for 1 h. The reaction mixture was then extracted with CHCl3 and the combined organic layers washed with water, brine, dried (Na2SO4), filtered and concentrated under vaccum. The crude product was purified by silica gel column chromatography using 2% acetone in chloroform to give 79 mg of the product of off-white solid; IR (KBr) 2959, 2243, 1573, 1455, 1263, 743 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 1.62-1.68 (m, 4H), 1.78-1.89 (m, 4H), 3.86 (s, 3H), 4.89 (br s, 1H), 6.90 (d, J=7.8 Hz, 1H), 7.03 (t, J=7.8 Hz, 1H), 7.11 (d, J=7.8 Hz, 1H), 7.23-7.28 (m, 1H), 7.35-7.44 (m, 2H), 7.59 (d, J=7.8 Hz, 1H), 7.87 (d, J=9.3 Hz, 2H), 8.06 (d, J=9.0 Hz, 1H), 8.19 (d, J=15.9 Hz,1H); APCI-MS (m/z) 438.21 (M+H)+.

Workup

  1. extractionThe reaction mixture was then extracted with CHCl3
  2. washthe combined organic layers washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vaccum
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fdb44ff8c3df4f759d026c8651bc3028
Source dataset
uspto-grants-2013_01
Patent number
US08344010B2

Reaction notes

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