Trifluoroacetic acid → HCID 91826322, compound

HRID 873976Notes

Reaction equation

HRID 873976 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[CH2:19][CH2:18]4)[C:11]=3[C:10](=[O:20])[N:9]2[C:21]2[CH:22]=[C:23]([N:31](C)[C:32](=O)OC(C)(C)C)[C:24]3[N:25]([C:27]([CH3:30])=[N:28][N:29]=3)[N:26]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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[CH2:18][CH2:19]4)[C:11]=3[C:10](=[O:20])[N:9]2[C:21]2[CH:22]=[C:23]([NH:31][CH3:32])[C:24]3[N:25]([C:27]([CH3:30])=[N:28][N:29]=3)[N:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86292782tert-butyl (6-(4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-6-oxopyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(methyl)carbamate

Product 1

HCID 91826322HCID 91826322, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (6-(4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-6-oxopyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(methyl)carbamate (Example 112) (200 mg, 0.364 mmol) in CH2Cl2 (4 mL) was added TFA (0.561 mL, 7.29 mmol) and the resulting mixture was stirred at RT for 2 hr. The reaction was quenched with a saturated aq. NaHCO3 solution and extracted with CH2Cl2. The combined organic layers were washed with a saturated aq. NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (CH2Cl2/MeOH 1-4%) followed by trituration in Et2O to afford the title product (130 mg, 0.290 mmol, 79% yield). tR: 4.73 min (HPLC 1); tR: 1.09 min (LC-MS 2); ESI-MS: 449 [M+H]+ (LC-MS 2); Rf=0.40 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01-1.08 (m, 2H) 1.19-1.26 (m, 2H) 1.90 (s, 3H) 2.45 (s, 3H) 2.85-2.94 (m, 3H) 3.77-3.84 (m, 1H) 6.41 (s, 1H) 7.03 (s, 1H) 7.31-7.36 (m, 2H) 7.37-7.42 (m, 2H) 8.01-8.10 (m, 1H).

Workup

  1. customThe reaction was quenched with a saturated aq. NaHCO3 solution
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with a saturated aq. NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography (CH2Cl2/MeOH 1-4%)

Sources & evidence

ORD record
ord-832b63f0854d4dbdbf5877f4ba5c2fb5
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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