Triethylamine → 3-[6-(8-Benzyl-2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-4-[(S)-2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-1H-pyridin-2-one

HRID 470311Notes

Reaction equation

HRID 470311 reaction equation
[CH2:1]([N:8]1[CH2:36][CH2:35][CH2:34][C:10]2([CH2:15][N:14]([C:16]3[CH:17]=[C:18]([CH3:33])[C:19]4[N:23]=[C:22]([C:24]5[C:25](=[O:31])[NH:26][CH:27]=[CH:28][C:29]=5Cl)[NH:21][C:20]=4[CH:32]=3)[CH2:13][CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:37][CH2:38][C@H:39]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[CH:42]=1)[OH:40].CCN(CC)CC>CCO>[CH2:1]([N:8]1[CH2:36][CH2:35][CH2:34][C:10]2([CH2:15][N:14]([C:16]3[CH:17]=[C:18]([CH3:33])[C:19]4[N:23]=[C:22]([C:24]5[C:25](=[O:31])[NH:26][CH:27]=[CH:28][C:29]=5[NH:37][CH2:38][C@H:39]([C:41]5[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[CH:42]=5)[OH:40])[NH:21][C:20]=4[CH:32]=3)[CH2:13][CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9855591(S)-2-amino-1-(3-chlorophenyl)ethanolHCID 1361066243-[6-(8-benzyl-2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-4-chloro-1H-pyridin-2-one

Product 1

HCID 1361067393-[6-(8-Benzyl-2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-4-[(S)-2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-1H-pyridin-2-oneYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[6-(8-benzyl-2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-4-chloro-1H-pyridin-2-one (17 mg, 0.034 mmol), (S)-2-amino-1-(3-chlorophenyl)-ethanol (29 mg, 0.17 mmol) and Et3N (34 mg, 0.34 mmol) in EtOH (0.5 mL) was heated at 80° C. for 16 h and then the reaction mixture was evaporated. The residue was purified by chromatography (25:1 CH2Cl2/MeOH) to afford the title compound (8 mg, 64%). 1H NMR (MeOH-d4) δ 1.28 (m, 2H), 1.50-1.83 (4H), 2.07-2.27 (2H), 2.48-2.61 (2H), 2.54 (s, 3H), 2.82-2.94 (2H), 3.041-3.23 (2H), 3.40-3.55 (2H), 3.59-3.73 (2H), 4.75 (m, 1H), 4.98 (m, 1H), 6.20 (d, J=6 Hz, 1H), 6.75 (s, 1H), 6.84 (s, 1H), 7.19-7.32 (8H), 7.35-7.42 (2H), 7.54 (s, 1H). ESI-MS m/z 637 (MH+).

Workup

  1. customthe reaction mixture was evaporated
  2. customThe residue was purified by chromatography (25:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-43d74595d4bf4cdb9a21cc1bf39c9206
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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