Trifluoroacetic acid → 2-Amino-4-(((1S)-1-(6-(4-aminocyclohex-1-en-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-6-methylpyrimidine-5-carbonitrile

HRID 2205630Notes

Reaction equation

HRID 2205630 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[C:21]2[CH2:26][CH2:25][CH:24]([NH:27]C(=O)OC(C)(C)C)[CH2:23][CH: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[C:21]2[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH:22]=2)[CH3:10])[C:5]([C:35]#[N:36])=[C:4]([CH3:37])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118215172tert-Butyl (4-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)cyclohex-3-en-1-yl)carbamate

Product 1

HCID 1182077862-Amino-4-(((1S)-1-(6-(4-aminocyclohex-1-en-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-6-methylpyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottom flask was charged with tert-butyl (4-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)cyclohex-3-en-1-yl)carbamate (0.079 g, 0.157 mmol), DCM (2 mL), and TFA (0.969 mL, 12.57 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated using a stream of nitrogen. A portion of the crude material was purified via preparative HPLC (acid mode, 5-25% ACN/water gradient). The product-containing fractions were dried in vacuo to give the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.81 (d, J=6.82 Hz, 3H), 0.97-1.16 (m, 1H), 1.30-1.51 (m, 2H), 1.57 (s, 3H), 1.63-1.94 (m, 3H), 2.66 (d, J=8.84 Hz, 1H), 3.07-3.15 (m, 3H), 4.69-4.88 (m, 1H), 5.02 (br s, 1H), 5.86 (d, J=3.03 Hz, 1H), 7.05 (d, J=3.03 Hz, 1H), 7.45 (d, J=4.04 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C22H26N8, 403. found 403.

Workup

  1. customThe solvent was evaporated
  2. customA portion of the crude material was purified via preparative HPLC (acid mode, 5-25% ACN/water gradient)
  3. customThe product-containing fractions were dried in vacuo

Sources & evidence

ORD record
ord-41ececfb4ea847f9b527c6f17a450612
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

Loading…