Methylamine → HCID 58654482, compound

HRID 1170536Notes

Reaction equation

HRID 1170536 reaction equation
[CH3:1][NH2:2].C(O[C:6](=[O:42])[CH2:7][CH:8]([NH:21][CH2:22][CH2:23][N:24]([CH2:32][C:33]1[CH:41]=[CH:40][C:36]2[O:37][CH2:38][O:39][C:35]=2[CH:34]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[N:10]=1)C>C1COCC1>[C:28]([O:27][C:25](=[O:26])[N:24]([CH2:32][C:33]1[CH:41]=[CH:40][C:36]2[O:37][CH2:38][O:39][C:35]=2[CH:34]=1)[CH2:23][CH2:22][NH:21][CH:8]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[N:10]=1)[CH2:7][C:6](=[O:42])[NH:2][CH3:1])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58654434HCID 58654434, compound

Product 1

HCID 58654482HCID 58654482, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (800 μL, 40 wt % aqueous) was added to a solution of 3-[2-(benzo[1,3]dioxol-5-ylmethyl-tert-butoxycarbonyl-amino)-ethylamino]-3-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-propionic acid ethyl ester (15 mg, 0.027 mmol) in THF (0.8 mL). The reaction mixture stirred at room temperature for 16 h then was concentrated under reduced pressure. The residue was purified using column chromatography (DCM to 9:1 DCM/MeOH) to afford 14 mg (96%) of benzo[1,3]dioxol-5-ylmethyl-{2-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methylcarbamoyl-ethylamino]-ethyl}-carbamic acid tert-butyl ester as a clear oil.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. customThe residue was purified

Sources & evidence

ORD record
ord-1f7945b87c58453fa5538e570ed80b32
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

Loading…