Nitrogen → HCID 49838065, compound

HRID 1189439Notes

Reaction equation

HRID 1189439 reaction equation
N#N.C(OC(=O)[N:9]([C:26]1[N:27]=[C:28]([CH2:31][N:32]2[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH3:38])=[N:33]2)[O:29][CH:30]=1)[C:10]([C:12]1[N:13]=[C:14]([CH:23]2[CH2:25][CH2:24]2)[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:37]([C:34]1[CH:35]=[CH:36][N:32]([CH2:31][C:28]2[O:29][CH:30]=[C:26]([NH:9][C:10]([C:12]3[N:13]=[C:14]([CH:23]4[CH2:24][CH2:25]4)[S:15][C:16]=3[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:11])[N:27]=2)[N:33]=1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 67128714HCID 67128714, compound

Product 1

HCID 49838065HCID 49838065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(3-acetyl-pyrazol-1-ylmethyl)-oxazol-4-yl]-(2-cyclopropyl-5-phenyl-thiazole-4-carbonyl)-carbamic acid tert-butyl ester (13 mg, 0.02 mmol) in dry CH2Cl2 (1.0 mL) was treated at 0° C. with trifluoroacetic acid (0.08 mL, 1.00 mmol). After stirring at rt for 16 h, the reaction mixture was quenched with sat. aq. NaHCO3, extracted with CH2Cl2 (3×10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (5:1→3:1 hept:EA) gave the title compound as a white solid. TLC: rf (1:1 hept-EA)=0.34. LC-MS-conditions 02: tR=1.08 min, [M+H]+=433.89.

Workup

  1. customthe reaction mixture was quenched with sat. aq. NaHCO3
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (5:1→3:1 hept:EA)

Sources & evidence

ORD record
ord-2b46043d65cb47d096a790847f3bdbad
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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