Trifluoroacetic acid → HCID 69308584, compound

HRID 2375318Notes

Reaction equation

HRID 2375318 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:11]=[C:10]([C:12](=[C:15]2[NH:19][C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][S:16]2)[C:13]#[N:14])[CH:9]=[CH:8][N:7]=1.[C:24]1(=O)[O:29][C:27](=[O:28])[CH2:26][CH2:25]1.CN1CCOCC1.C(O)(C(F)(F)F)=O>CC(N(C)C)=O.C(Cl)Cl.CCOCC.O>[C:20]([C:18]1[NH:19][C:15](=[C:12]([C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][N:1]3[C:27](=[O:28])[CH2:26][CH2:25][C:24]3=[O:29])[N:11]=2)[C:13]#[N:14])[S:16][CH:17]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7922Succinic anhydrideHCID 79724-MethylmorpholineHCID 67068560HCID 67068560, compound

Product 1

HCID 69308584HCID 69308584, compoundYield 140.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
250 °C

Procedure

To a suspension of {2-[(3-aminopropyl)amino]pyrimidin-4-yl}(4-tert-butyl-1,3-thiazol-2(3H)-ylidene)acetonitrile (200 mg, 0.61 mmol) in DMA in a microwave tube (X2) were added succinic anhydride (122 mg, 1.21 mmol) and NMM (0.133 mL, 1.21 mmol) and after sonication the solution was heated up to 250° C. on normal absorption for 15 min. Both tubes were gathered and 10 mL of water were added then the suspension was left at 4° C. for ON. The solid obtained was filtered off through paper and washed with water (3×) then dried under vacuum at 40° C. for 5 days, affording the crude title compound as a brown powder. The solid was taken up in DCM then an excess TFA was added. To the black solution was added ether and the suspension was left at 4° C. for 2 h. The precipitate formed was filtered off then washed with ether (3×), affording 353.9 mg of the title compound as a TFA salt (HPLC (max plot) 92%).

Workup

  1. customafter sonication the solution
  2. waitthe suspension was left at 4° C. for ON
  3. customThe solid obtained
  4. filtrationwas filtered off through paper
  5. washwashed with water (3×)
  6. customthen dried under vacuum at 40° C. for 5 days
  7. customaffording the crude title compound as a brown powder
  8. customThe precipitate formed
  9. filtrationwas filtered off
  10. washthen washed with ether (3×)

Sources & evidence

ORD record
ord-269a45e5d47b4a1d9cdd3fafa981bc20
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

Loading…