Methanol → HCID 118598582, compound

HRID 1050402Notes

Reaction equation

HRID 1050402 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13](CC3C=CC(OC)=CC=3)[C:12]([C:25]([NH:27]CC3C=CC(OC)=CC=3)=[O:26])=[C:11]([Cl:37])[CH:10]=2)[CH:3]=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.CO>ClCCl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14](=[O:15])[NH:13][C:12]([C:25]([NH2:27])=[O:26])=[C:11]([Cl:37])[CH:10]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 118598764HCID 118598764, compound

Product 1

HCID 118598582HCID 118598582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-((6-aminopyrimidin-4-yl)amino)-3-chloro-N,1-bis(4-methoxybenzyl)-6-oxo-1,6-dihydropyridine-2-carboxamide (6, 0.40 g, 0.77 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (20 mL) and trifluoromethanesulfonic acid (1 mL) at 0° C. The reaction mixture was stirred at 70° C. for 2 h. After completion, the reaction mixture was concentrated and basified by aq. ammonia at 0° C. The precipitate obtained was collected by filtration, washed with water and dried to obtain the crude. The crude was stirred with methanol, filtered, washed with pentane and dried to afford 5-((6-aminopyrimidin-4-yl)amino)-3-chloro-6-oxo-1,6-dihydropyridine-2-carboxamide (Cpd. No. 214) as yellow solid. Yield: 0.035 g, 16%; MS (ESI) m/z 281.05 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.66 (s, 1H), 8.50 (s, 1H), 8.17 (s, 1H), 7.92 (s, 1H), 7.86 (s, 1H), 6.53 (s, 2H), 6.18 (s, 1H).

Workup

  1. concentrationAfter completion, the reaction mixture was concentrated
  2. custombasified by aq. ammonia at 0° C
  3. customThe precipitate obtained
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried
  7. customto obtain the crude
  8. filtrationfiltered
  9. washwashed with pentane
  10. customdried

Sources & evidence

ORD record
ord-9331246664fd4e14b5e2a806da313571
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…