Triethylamine → HCID 67191083, compound

HRID 515334Notes

Reaction equation

HRID 515334 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH3:18][NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(N(CC)CC)C>ClCCl>[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:19]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH3:18])=[O:14])=[CH:15][CH:16]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acid

Product 1

HCID 67191083HCID 67191083, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propanephosphonic acid cyclic anhydride (3.74 mL, 6.40 mmol) was added to a solution of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (500 mg, 2.134 mmol), tert-butyl 4-(methylamino)piperidine-1-carboxylate (457 mg, 2.134 mmol) and triethylamine (1.19 mL, 8.54 mmol) in dichloromethane (20 mL). The mixture was stirred at ambient temp for 3.5 hours and then concentrated under reduced pressure. The crude material was purified by silica chromatography (eluting with a solvent gradient from 2.5% methanol/97.5% dichloromethane to 5% methanol/95% dichloromethane) to afford the title compound (440 mg). MS (ESI) m/z 431.5 [M+H]+

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude material was purified by silica chromatography (
  3. washeluting with a solvent gradient from 2.5% methanol/97.5% dichloromethane to 5% methanol/95% dichloromethane)

Sources & evidence

ORD record
ord-9c37fd579d414a9883a957d7a3419334
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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