Diisopropylethylamine → HCID 178461896, compound

HRID 409024Notes

Reaction equation

HRID 409024 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[S:14][CH:15]=[CH:16][C:11]3=[CH:10][C:9]=2[C@@H:17]([NH2:19])[CH3:18])[CH:5]=[CH:6][CH:7]=1.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[NH:23][CH:24]=[N:25]2.CCN(C(C)C)C(C)C>C(O)CCC>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[S:14][CH:15]=[CH:16][C:11]3=[CH:10][C:9]=2[C@@H:17]([NH:19][C:21]2[N:29]=[CH:28][N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][NH:25]3)[CH3:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 68622748HCID 68622748, compound

Product 1

HCID 178461896HCID 178461896, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

In a reaction flask was combined (1S)-1-(6-(3-fluorophenyl)thieno[2,3-b]pyridin-5-yl)ethanamine (39 mg, 143 μmol), 6-chloropurine (24 mg, 158 μmol), Hunig's Base (38 μL, 215 μmol) and n-butanol (1.5 mL). The solution was heated to 110° C. After 24 h, the solvent was removed and the residue purified by column chromatography using a 0-70% gradient of (90:9:1 CH2Cl2:MeOH:NH4OH) in CH2Cl2 to afford N—((S)-1-(6-(3-fluorophenyl)thieno[2,3-b]pyridin-5-yl)ethyl)-9H-purin-6-amine. 1H NMR (400 MHz, DMSO-d6) δ 12.90 (br s, 1H), 8.51 (br s, 1H), 8.34 (br s, 1H), 8.10 (m, 2H), 7.88 (d, J=5.9 Hz, 1H), 7.59 (m, 3H), 7.45 (d, J=5.9 hz, 1H), 7.30 (br t, J=6.3 Hz, 1H), 5.60 (br s, 1H), 1.44 (br d, J=5.1 Hz, 3H) ppm. LC/MS (M+1, found=391.1).

Workup

  1. customIn a reaction flask was combined
  2. customthe solvent was removed
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-8c5c2d705d984cb8871d3a9b988dfce0
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

Loading…