Trifluoroacetic acid → HCID 118207763, compound

HRID 2205631Notes

Reaction equation

HRID 2205631 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:16]=[C:15]3[CH:17]=[CH:18][N:19]([CH3:20])[C:14]3=[CH:13][C:12]=2[CH:21]2[CH2:26][CH2:25][CH:24]([NH:27]C(=O)OC(C)(C)C)[CH2:23][CH2:22]2)[CH3:10])[C:5]([C:35]#[N:36])=[C:4]([CH3:37])[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:16]=[C:15]3[CH:17]=[CH:18][N:19]([CH3:20])[C:14]3=[CH:13][C:12]=2[CH:21]2[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]2)[CH3:10])[C:5]([C:35]#[N:36])=[C:4]([CH3:37])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118215177HCID 118215177, compound

Product 1

HCID 118207763HCID 118207763, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A scintillation vial was charged with (S)-tert-butyl (4-(5-(1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)cyclohexyl)carbamate (0.012 g, 0.024 mmol), DCM (1 mL), and TFA (0.916 mL, 11.89 mmol). The reaction mixture was stirred at room temperature for 45 minutes. The solvent was evaporated via a stream of nitrogen. The crude product was dissolved in a mixture of DMSO and MeOH (1:1) and was purified by preparative HPLC (basic mode, 25-50% ACN/H2O gradient). The product-containing fractions were dried in vacuo to give the title compound as a white solid (5 mg, 53%). 1H NMR (400 MHz, CD3OD) δ ppm 1.31 (br s, 1H), 1.55 (d, J=6.57 Hz, 5H), 1.62-1.82 (m, 2H), 1.85-2.04 (m, 7H), 2.05-2.26 (m, 2H), 2.36 (s, 3H), 2.94-3.12 (m, 2H), 3.84-3.89 (m, 3H), 5.77-5.97 (m, 1H), 6.57 (d, J=4.72 Hz, 1H), 7.46 (d, J=4.49 Hz, 1H), 7.94 (s, 1H), 7.78 (s, J=64.10 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C22H28N8, 405. found 405.

Workup

  1. customThe solvent was evaporated via a stream of nitrogen
  2. dissolutionThe crude product was dissolved in a mixture of DMSO and MeOH (1:1)
  3. customwas purified by preparative HPLC (basic mode, 25-50% ACN/H2O gradient)
  4. customThe product-containing fractions were dried in vacuo

Sources & evidence

ORD record
ord-7c2a4490c6c94fb2bd8adef89a02326f
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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