Trifluoroacetic acid → HCID 73056231, compound

HRID 2284426Notes

Reaction equation

HRID 2284426 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:27]=[N:26][C:25]4[C:24]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)=[N:23][C:22]([C:34]5[CH:35]=[N:36][C:37]([NH:40]C(=O)OC(C)(C)C)=[N:38][CH:39]=5)=[N:21][C:20]=4[CH:19]=3)[CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:40][C:37]1[N:36]=[CH:35][C:34]([C:22]2[N:23]=[C:24]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:25]3[N:26]=[CH:27][C:18]([C:14]4[CH:13]=[C:12]([NH:11][S:8]([C:5]5[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=5)(=[O:9])=[O:10])[CH:17]=[CH:16][CH:15]=4)=[CH:19][C:20]=3[N:21]=2)=[CH:39][N:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86710188HCID 86710188, compound

Product 1

HCID 73056231HCID 73056231, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL flask, tert-butyl (5-(7-(3-(4-fluorophenylsulfonamido)phenyl)-4-morpholino-pyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.06 g, 0.00009 mol) and DCM (9 mL) were added. To the same reaction vessel, trifluoroacetic acid (0.5 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The volatiles were evaporated under reduced pressure to provide the residue. The residue was washed with ether and was dissolved in 10% methanol in DCM. The organic layer was basified with saturated sodium bicarbonate solution (pH 8.0). The organic layer was washed with water, brine, dried over sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was washed with methanol and diethyl ether to provide the solid. The solid was dried under high vacuum to provide the title compound (0.031 g, 60%). 1H NMR (400 MHz, DMSO-d6): δ 10.57 (s, 1H), 9.20 (s, 2H), 8.92 (d, J=2.4 Hz, 1H), 8.16 (d, J=2.4 Hz, 1H), 7.90-7.87 (m, 2H), 7.63 (d, J=7.6 Hz, 1H), 7.55 (br s, 1H), 7.46-7.40 (m, 3H), 7.22 (br s, 2H), 7.20 (s, 1H) 4.52 (br s, 4H), 3.84 (t, J=4.4 Hz, 4H). LC-MS (ESI): Calculated mass: 558.1; Observed mass [M+H]+: 558.9 (RT=1.19 min).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customto provide the residue
  3. washThe residue was washed with ether
  4. dissolutionwas dissolved in 10% methanol in DCM
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customto provide the crude product
  9. washThe crude product was washed with methanol and diethyl ether
  10. customto provide the solid
  11. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-7f514041bad849d6ade73eb224c59e34
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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