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

HRID 470312Notes

Reaction equation

HRID 470312 reaction equation
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:13][C:12]2[CH:14]=[C:15]([N:19]3[CH2:24][CH2:23][CH2:22][C:21]4([CH2:29][CH2:28][CH2:27][NH:26][CH2:25]4)[CH2:20]3)[CH:16]=[C:17]([CH3:18])[C:11]=2[N:10]=1.[NH2:30][CH2:31][C@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)[OH:33].CCN(CC)CC>CCO>[Cl:40][C:36]1[CH:35]=[C:34]([C@H:32]([OH:33])[CH2:31][NH:30][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:9]2[NH:13][C:12]3[CH:14]=[C:15]([N:19]4[CH2:24][CH2:23][CH2:22][C:21]5([CH2:29][CH2:28][CH2:27][NH:26][CH2:25]5)[CH2:20]4)[CH:16]=[C:17]([CH3:18])[C:11]=3[N:10]=2)[CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9855591(S)-2-amino-1-(3-chlorophenyl)ethanolHCID 1361069934-Chloro-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one

Product 1

HCID 1361070274-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-oneYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-Chloro-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one (16 mg, 0.039 mmol), (S)-2-amino-1-(3-chlorophenyl)-ethanol (20 mg, 0.117 mmol) and Et3N (16 mg, 0.156 mmol) in EtOH (0.5 mL) was heated at 80° C. for 16 h. After it was cooled to room temperature, the reaction mixture was filtered to furnish yellow solid that was washed with MeOH (3×3 mL). The yellow solid then was mixed with 3 mL MeOH and the mixture was heated at 100° C. for 1 h. After it was cooled to room temperature, the mixture was filtered to furnish yellow solid that was washed with MeOH (3×2 mL) to afford the title compound (10 mg, 47%). ESI-MS m/z 547 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto furnish yellow solid
  3. washthat was washed with MeOH (3×3 mL)
  4. additionThe yellow solid then was mixed with 3 mL MeOH
  5. temperaturethe mixture was heated at 100° C. for 1 h
  6. temperatureAfter it was cooled to room temperature
  7. filtrationthe mixture was filtered
  8. customto furnish yellow solid
  9. washthat was washed with MeOH (3×2 mL)

Sources & evidence

ORD record
ord-53bc78b49d664e8f91dfbaca9acfe72e
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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