Trifluoroacetic acid → HCID 68455384, compound

HRID 500645Notes

Reaction equation

HRID 500645 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[CH:15]=[CH:14]4)[C:3]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:16]1[C:17]2[C:13](=[CH:12][C:11]([C:10]3[C:3]4[C:4](=[N:5][CH:6]=[N:7][C:2]=4[NH2:1])[N:8]([CH:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)[N:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68456420HCID 68456420, compound

Product 1

HCID 68455384HCID 68455384, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 201B (1.28 g, 2.3 mmol) in anhydrous CH2Cl2 (30 ml) was cooled in an ice bath and TFA (7.5 ml) was added dropwise under inert atmosphere. After stirring 15 min the ice bath was removed and the reaction allowed to warm to ambient temperature while stirring 1 hr. The reaction was concentrated and the residue dissolved in 1M-HCl. The solution washed with EtOAc, basified with 1M-Na2CO3 (pH 9-10) and extracted with 5% MeOH/CH2Cl2 (3×100 ml). The combined extracts were dried over Na2SO4, filtered, concentrated and dried to give the title compound as a tan foam (70%). MS (ESI+) m/e 458 (M+H)+; 1H NMR (300 MHz, DMSO-d6) 8.22 (s, 1H), 7.88 (s, 1H), 7.55 (m, 3H), 7.42 (d, 1H), 7.33 (m, 1H), 7.25 (m, 1H), 6.74 (dd, 1H), 6.67 (d, 1H), 6.24 (vbr s, 3H), 5.59 (s, 2H), 4.73 (m, 1H), 3.07 (m, 2H), 2.63 (m, 2H), 2.04 (m, 2H), 1.82 (m, 2H).

Workup

  1. customwas removed
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue dissolved in 1M-HCl
  4. washThe solution washed with EtOAc
  5. extractionextracted with 5% MeOH/CH2Cl2 (3×100 ml)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-5a167388926641c09ae24d06081a6d95
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

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