Methylamine → HCID 178485585, compound

HRID 1873902Notes

Reaction equation

HRID 1873902 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:10][C:9]=2[C:25]([O:27]CC)=O)=[CH:4][CH:3]=1.[CH3:30][NH2:31]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[N:10][C:9]=2[C:25](=[O:27])[NH:31][CH3:30])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178470251HCID 178470251, compound

Product 1

HCID 178485585HCID 178485585, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

(S)-ethyl 5-(4-bromophenyl)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazole-4-carboxylate (1 g, 2.1 mmol) was dissolved in 2M methylamine in MeOH (35 mL) and heated in a pressure vessel at 70° C. for 48 h. The reaction mixture was concentrated and the residue applied to a Biotage 25 m silica gel cartridge and eluted by 10-100% gradient, ethyl acetate/Hex to give 556 mg (57%). 1H NMR (300 MHz, DMSO-d6) δ 12.5 (br.s, 1H), 7.86-7.82 (m, 1H), 7.77 (d, J=8.4 Hz, 2H), 7.61 (d, J=8.7 Hz, 2H), 4.83-4.70 (m, 1H), 3.69-3.52 (br.s, 1H), 3.42-3.32 (m, 1H), 2.71 (d, 4.8 Hz, 3H), 2.30-1.78 (m, 4H), 1.19-1.14 (m, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washeluted by 10-100% gradient, ethyl acetate/Hex
  3. customto give 556 mg (57%)

Sources & evidence

ORD record
ord-92f016a50c6c48eea18e50c548dec72e
Source dataset
uspto-grants-2012_11
Patent number
US08303944B2

Reaction notes

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