Trifluoroacetic acid → HCID 91826339, compound

HRID 873998Notes

Reaction equation

HRID 873998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([CH:17]4[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]4)[C:11]=3[C:10](=[O:28])[N:9]2[C:29]2[CH:34]=[C:33]([CH3:35])[C:32](=[O:36])[N:31]([CH3:37])[CH:30]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:19]1[CH2:18][CH:17]([N:12]2[C:11]3[C:10](=[O:28])[N:9]([C:29]4[CH:34]=[C:33]([CH3:35])[C:32](=[O:36])[N:31]([CH3:37])[CH:30]=4)[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:15]=3[C:14]([CH3:16])=[N:13]2)[CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117702682HCID 117702682, compound

Product 1

HCID 91826339HCID 91826339, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-methyl-6-oxo-5,6-dihydropyrrolo[3,4-c]pyrazol-1(4H)-yl)azetidine-1-carboxylate (Step 138.1a) (280 mg, 0.534 mmol) in CH2Cl2 (4 mL) was added TFA (0.412 mL, 5.34 mmol). The reaction mixture was stirred for 1 h at rt, quenched by addition of a saturated aqueous solution of NaHCO3, and extracted with CH2Cl2. The combined organic layers were dried on Na2SO4 and evaporated. The residue was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-4%) to afford 200 mg of the title compound as a colorless solid. tR: 0.66 min (LC-MS 2); ESI-MS: 424.1 [M+H]+ (LC-MS 2); Rf=0.09 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.91 (s, 3H) 1.94 (s, 3H) 3.35 (s, 3H) 3.70-3.78 (m, 2H) 4.06-4.14 (m, 2H) 5.26-5.37 (m, 1H) 6.07 (br. s, 1H) 7.23-7.29 (m, 2H) 7.34-7.40 (m, 3H) 7.71 (d, J=2.74 Hz, 1H).

Workup

  1. customquenched by addition of a saturated aqueous solution of NaHCO3
  2. extractionextracted with CH2Cl2
  3. customThe combined organic layers were dried on Na2SO4
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-4%)

Sources & evidence

ORD record
ord-010ea8de5bed420f847db27406d61df1
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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