Triethylamine → HCID 178440846, compound

HRID 2171311Notes

Reaction equation

HRID 2171311 reaction equation
[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[NH:5][CH:4]=[C:3]1[C:11]([OH:13])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:45][C:46]1[C:47]([C:57]([CH3:60])([CH3:59])[CH3:58])=[CH:48][C:49]([C:53]([CH3:56])([CH3:55])[CH3:54])=[C:50]([OH:52])[CH:51]=1>C1COCC1>[C:57]([C:47]1[CH:48]=[C:49]([C:53]([CH3:56])([CH3:55])[CH3:54])[C:50]([OH:52])=[CH:51][C:46]=1[NH:45][C:11]([C:3]1[C:2](=[O:1])[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[NH:5][CH:4]=1)=[O:13])([CH3:60])([CH3:58])[CH3:59]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441762265-Amino-2,4-di-tert-butylphenolHCID 178524787HCID 178524787, compound

Product 1

HCID 178440846HCID 178440846, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a vial charged with 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid (50 mg, 0.28 mmol) and HATU (117 mg, 0.31 mmol) was added 2 mL of THF followed by triethylamine (85 mg, 0.84 mmol). The reaction mixture was allowed to stir for 10 minutes at room temperature, upon which 5-amino-2,4-di-tert-butylphenol (62 mg, 0.28 mmol) was added and the reaction was heated at 65° C. for 16 h. After 16 h, the reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2 0 (0.05% TFA)). LC/MS (10-99% CH3CN/0.05% TFA in H2O/0.05% TFA gradient over 3 min) to give N-(2,4-di-tert-butyl-5-hydroxyphenyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxamide; M+H m/z 383.3, retention time 1.71 minutes. 1H NMR (400.0 MHz, DMSO) δ 13.48 (s, 1H), 10.68 (s, 1H), 9.24 (s, 1H), 8.78 (s, 1H), 8.06 (d, J=2.0 Hz, 1H), 7.17 (s, 1H), 7.13 (s, 1H), 6.41 (d, J=2.0 Hz, 1H), 1.36 (d, J=4.5 Hz, 18H).

Workup

  1. additionwas added
  2. temperaturethe reaction was cooled to room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2 0 (0.05% TFA))

Sources & evidence

ORD record
ord-0218ddad783e427d8ac3ab2531f00036
Source dataset
uspto-grants-2015_06
Patent number
US09051324B2

Reaction notes

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