Trifluoroacetic acid → HCID 117843746, compound

HRID 2209081Notes

Reaction equation

HRID 2209081 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[CH:8]1([N:11]2[C:15]3[C:16]([O:34][C@@H:35]([C@H:37]4[CH2:41][NH:40][C:39](=[O:42])[CH2:38]4)[CH3:36])=[N:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[C:22]([O:32][CH3:33])[CH:21]=4)=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH2:10][CH2:9]1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:3]([N:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([C:18]3[N:17]=[C:16]([O:34][C@@H:35]([C@H:37]4[CH2:41][NH:40][C:39](=[O:42])[CH2:38]4)[CH3:36])[C:15]4[N:11]([CH:8]5[CH2:10][CH2:9]5)[CH:12]=[N:13][C:14]=4[CH:19]=3)=[CH:21][C:22]=2[O:32][CH3:33])[CH2:27][CH2:28]1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117843591HCID 117843591, compound

Product 1

HCID 117843746HCID 117843746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an appropriate sized vial the trifluoroacetic acid salt of (R)-4-((R)-1-((3-cyclopropyl-6-(3-methoxy-4-(piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: 3.51 (80 mg, 0.085 mmol) and triethylamine (52 mg, 0.51 mmol) were dissolved in DCM (4 mL). To this mixture acetic anhydride (10.5 mg, 0.1 mmol) was added and the mixture was stirred at room temperature for 30 min. After reaction was complete the solution was concentrated under reduced pressure and the residue was purified via prep HPLC (2-65% acetonitrile in water, 0.1% trifluoroacteic acid buffer) to provide (R)-4-((R)-1-((6-(4-(4-acetylpiperazin-1-yl)-3-methoxyphenyl)-3-cyclopropyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: 3.52 as its trifluoroacetic acid salt.

Workup

  1. customAfter reaction
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified via prep HPLC (2-65% acetonitrile in water, 0.1% trifluoroacteic acid buffer)

Sources & evidence

ORD record
ord-a434fc2bc8394e7c881c66fb9afce7dd
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…