Trifluoroacetic acid → HCID 73056229, compound

HRID 2284416Notes

Reaction equation

HRID 2284416 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[O:14][C:13]([C:15]3[CH:24]=[N:23][C:22]4[C:21]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[N:20][C:19]([C:31]5[CH:32]=[N:33][C:34]([NH:37]C(=O)OC(C)(C)C)=[N:35][CH:36]=5)=[N:18][C:17]=4[CH:16]=3)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:37][C:34]1[N:33]=[CH:32][C:31]([C:19]2[N:20]=[C:21]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:22]3[N:23]=[CH:24][C:15]([C:13]4[O:14][C:10]([C:8]([N:5]5[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]5)=[O:9])=[CH:11][CH:12]=4)=[CH:16][C:17]=3[N:18]=2)=[CH:36][N:35]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86710182HCID 86710182, compound

Product 1

HCID 73056229HCID 73056229, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL flask, tert-butyl (5-(7-(5-(4-methylpiperazine-1-carbonyl)furan-2-yl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.06 g, 0.0001 mol) and DCM (10 mL) were added. To the reaction mixture, trifluoroacetic acid (0.076 mL, 0.001 mol) was added. The reaction mixture was stirred at room temperature for 3 hours. The volatiles were evaporated under reduced pressure to provide a residue. The residue was basified to pH 8.0 with saturated sodium bicarbonate solution and extracted with DCM. The organic layer was washed with water and brine, dried over sodium sulfate and evaporated to provide the crude product. The crude product was purified by preparative TLC (5% methanol in chloroform) to provide the title compound (0.01 g, 20%). 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 2H), 9.02 (d, J=2.4; H, 1H), 8.35 (d, J=2.0 Hz, 1H), 7.23 (d, J=3.6 Hz, 1H), 7.08 (d, J=3.6 Hz, 1H), 5.40 (br s, 2H), 4.63 (br s, 4H), 3.99 (t, J=4.8 Hz, 8H), 2.61 (t, J=4.4 Hz, 4H), 2.43 (s, 3H): LC-MS (ESI): Calculated mass: 501.2; Observed mass [M+H]+: 502.0 (RT=0.08 min).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customto provide a residue
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto provide the crude product
  8. customThe crude product was purified by preparative TLC (5% methanol in chloroform)

Sources & evidence

ORD record
ord-b1d2211fd0fb46fd9de0fa16b3182673
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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