Triethylamine → 4-Chloro-6-(1-methyl-piperidin-4-yl)-2-[4-(1-methyl-2-thiophen-2-yl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-1H-1,3,6-triaza-s-indacene-5,7-dione

HRID 1771903Notes

Reaction equation

HRID 1771903 reaction equation
[Cl:1][C:2]1[C:13]2[C:12](=[O:14])[N:11]([CH:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[C:10](=[O:22])[C:9]=2[CH:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:23]1[C:24](=[O:43])[NH:25][CH:26]=[CH:27][C:28]=1NCC(O)COC1C=CC(C)=CC=1C)[NH:6]2.[CH3:44][CH:45]([NH2:52])[CH2:46][C:47]1[S:48][CH:49]=[CH:50][CH:51]=1.CCN(CC)CC>CCO>[Cl:1][C:2]1[C:13]2[C:12](=[O:14])[N:11]([CH:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[C:10](=[O:22])[C:9]=2[CH:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:23]1[C:24](=[O:43])[NH:25][CH:26]=[CH:27][C:28]=1[NH:52][CH:45]([CH3:44])[CH2:46][C:47]1[S:48][CH:49]=[CH:50][CH:51]=1)[NH:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64841332-(2-Aminopropyl)thiopheneHCID 1363511614-Chloro-2-{4-[3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione

Product 1

HCID 1363340154-Chloro-6-(1-methyl-piperidin-4-yl)-2-[4-(1-methyl-2-thiophen-2-yl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-1H-1,3,6-triaza-s-indacene-5,7-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-{4-[3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione (18 mg, 0.04 mmol), 1-methyl-2-thiophen-2-yl-ethylamine (8.5 mg, 0.06 mmol) and Et3N (0.2 mL, 1.43 mmol) in EtOH (1.0 mL) was heated at 80° C. for 17 h and then concentrated to result a residue which was subjected to HPLC purification to furnish the title compound in TFA salt form (6.73 mg, 25%). 1H NMR (DMSO-d6) δ 1.36 (d, J=6 Hz, 3H, CH3), 1.95 (m, 2H), 2.52 (m, 2H), 2.74 (s, 3H, CH3), 3.02-3.22 (4H), 3.45 (m, 2H), 4.08 (m, 1H), 4.28 (m, 1H), 6.19 (d, J=8 Hz, 1H), 6.89 (m, 1H), 7.00 (m, 1H), 7.29 (m, 1H), 7.39 (m, 1H), 8.09 (s, 1H), 11.01 (d, J=8 Hz, 1H), 11.35 (d, J=6 Hz, 1H); ESI-MS m/z 551.3 (MH+).

Workup

  1. concentrationconcentrated
  2. customto result a residue which
  3. customwas subjected to HPLC purification

Sources & evidence

ORD record
ord-d0f72ba269c943128f6d9181034ef6c6
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

Loading…