Trifluoroacetic acid → HCID 118599020, compound

HRID 1050377Notes

Reaction equation

HRID 1050377 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:27](=[O:28])[N:13]3[CH2:14][CH2:15][CH2:16][N:17](CC4C=CC=CC=4)[C:18](=[O:19])[C:12]3=[C:11]([CH3:29])[CH:10]=2)[CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:27](=[O:28])[N:13]3[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[C:12]3=[C:11]([CH3:29])[CH:10]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 118598727HCID 118598727, compound

Product 1

HCID 118599020HCID 118599020, compound

Conditions

Temperature
150 °C

Procedure

A vial was charged with 8-((6-aminopyrimidin-4-yl)amino)-2-benzyl-10-methyl-2,3,4,5-tetrahydropyrido[1,2-a][1,4]diazepine-1,7-dione (8, 0.3 g, 76.9 mmol) and trifluoroacetic acid (7.0 mL) was added and the reaction mixture was heated under microwave at 150° C. for 20 min. TLC showed completion of the reaction and the mixture was cooled to ambient temperature and this was then basified with aqueous sodium bicarbonate solution and extracted with 5% methanol/dichloromethane (3×200 mL). The organic layer was dried over sodium sulfate and solvent was removed under reduced pressure to afford 8-((6-aminopyrimidin-4-yl)amino)-10-methyl-2,3,4,5-tetrahydropyrido[1,2-a][1,4]diazepine-1,7-dione (Cpd. No. 147) as a brown solid. Yield: 0.06 g, 26%; MS (ESI) m/z 301.15 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.44 (m, 2H), 8.15 (s, 1H), 6.52 (m, 2H), 6.13 (s 1H), 5.05 (m, 1H), 3.17 (m, 2H), 2.95 (m, 1H), 2.13 (s, 3H), 1.87 (m, 2H).

Workup

  1. additionwas added
  2. customcompletion of the reaction
  3. temperaturethe mixture was cooled to ambient temperature
  4. extractionextracted with 5% methanol/dichloromethane (3×200 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-dac8f6769d2d4733b73136c0926a3f60
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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