Diisopropylethylamine → HCID 58464823, compound

HRID 1185379Notes

Reaction equation

HRID 1185379 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[NH2:8][C:9]1[C:10]([C:16](O)=[O:17])=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[NH2:8][C:9]1[C:10]([C:16]([NH:7][C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:17])=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 47709901-methyl-1H-pyrazol-4-amineHCID 454804523-Amino-6-bromopicolinic acid

Product 1

HCID 58464823HCID 58464823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round bottom flask containing 1-methyl-1H-pyrazol-4-amine (700 mg, 7.0 mmol), 3-amino-6-bromopicolinic acid (1.86 g, 8.5 mmol) and PyBop (4.12 g, 8.0 mmol) was added methylene chloride (30 mL) and diisopropylethylamine (3.8 mL, 21.6 mmol). The reaction mixture was stirred for 24 hr at room temperature and the reaction was monitored by LCMS. Upon completion of the reaction, the solvent was distilled off and the crude material was purified via flash chromatography, heptane/ethyl acetate 0% to 100% to afford a yellow solid. A fraction of it was purified via reverse phase HPLC to afford 317. 1H NMR (400 MHz, DMSO) δ 10.25 (s, 1H), 8.03 (s, 1H), 7.70 (s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.19 (d, J=8.7 Hz, 1H), 7.02 (br, 2H), 3.81 (s, 3H). MS (ESI) m/z: 296.0/298.0 [M+H+].

Workup

  1. customUpon completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe crude material was purified via flash chromatography, heptane/ethyl acetate 0% to 100%
  4. customto afford a yellow solid
  5. customA fraction of it was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-8bf6533706d14ab09b7b53406a480128
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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