Triethylamine → HCID 46206218, compound

HRID 714954Notes

Reaction equation

HRID 714954 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C:11]1[O:12][C:13]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:23][CH:24]=2)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=1.C(N(CC)CC)C.[CH3:38][N:39]=[C:40]=[O:41]>C(Cl)Cl>[C:16]([C:14]1[N:15]=[C:11]([C:5]2[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:4]=2[F:3])[O:12][C:13]=1[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([C:40]([NH:39][CH3:38])=[O:41])[CH2:29][CH2:30]2)=[N:21][CH:20]=1)(=[O:17])[NH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 68521813HCID 68521813, compound

Product 1

HCID 46206218HCID 46206218, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(2,6-difluorophenyl)-5-(6-(piperazin-1-yl)pyridin-3-yl)oxazole-4-carboxamide dihydrochloride (0.060 g, 0.13 mmol) in DCM (3 mL) was added triethylamine (40 uL, 0.29 mmol) followed by methyl isocyanate (12 uL, 0.20 mmol). The resulting solution was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was purified by preparative HPLC and then by SPE using a MP-TsOH resin (500 mg) cartridge to afford 4-(5-(4-carbamoyl-2-(2,6-difluorophenyl)oxazol-5-yl)pyridin-2-yl)-N-methylpiperazine-1-carboxamide (0.0057 g, 0.013 mmol, 10%) as a yellow solid. 1H NMR (DMSO) 2.58 (3H, d), 3.40 (4H, m), 3.61 (4H, m), 6.54 (1H, br. q), 6.99 (1H, d), 7.38 (2H, t), 7.65 (1H, br. s), 7.67 (1H, br. s), 7.72 (1H, m), 8.37 (1H, dd), 8.95 (1H, d). LCMS (2) Rt: 2.27 min; m/z (ES+) 443.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f19c1cb06be64dc38bb3d5b0b3d128b2
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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