Hydrochloric Acid → HCID 49780164, compound

HRID 929505Notes

Reaction equation

HRID 929505 reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:26])[NH:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:6][CH:5]=1.Cl>CO>[NH:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:27])[F:28])=[CH:5][CH:6]=2)=[O:26])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49780163HCID 49780163, compound

Product 1

HCID 49780164HCID 49780164, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 41 (2.02 g, 5.0 mmol) was treated with 1M HCl in methanol (35 mL) and refluxed for 3 hours. The solvent was evaporated and the residue diluted with 1N NaOH. The resulting precipitate was removed by filtration and further dried under high vacuum to give intermediate 42 (1.35 g, 89%) as a white solid: Mp 169-173° C. 1H NMR (500 MHz, DMSO-d6) δ 8.49 (s, 1H), 7.46 (d, J=9.0 Hz, 2H), 7.21 (d, J=8.6 Hz, 2H), 6.15 (d, J=7.7 Hz, 1H), 3.55-3.45 (m, 1H), 2.89 (td, J=12.8, 3.5 Hz, 2H), 2.49-2.45 (m, 2H), 2.13 (s, 1H), 1.74 (dd, J=12.4, 2.4 Hz, 2H), 1.21 (dq, J=11.7, 3.7 Hz, 2H). HRMS calculated for C13H16F3N3O2−H+ 302.1117. found (ESI(−), [M−H]) 302.1114.

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe solvent was evaporated
  3. additionthe residue diluted with 1N NaOH
  4. customThe resulting precipitate was removed by filtration
  5. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-995633b882af43ddaa081473af61d784
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

Loading…