4-Methylmorpholine → HCID 59447712, compound

HRID 1678440Notes

Reaction equation

HRID 1678440 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=[C:5]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=O)[CH2:17][CH2:16]2)[N:4]=1.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:5]3[N:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:6]=3)[CH2:20][CH2:19]2)=[O:23])=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 67338015HCID 67338015, compound

Product 1

HCID 59447712HCID 59447712, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[4-(methylamino)-6-phenyl-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (80.0 mg, 0.255 mmol), 4-chlorobenzylamine (32.0 mg, 0.255 mmol), EDCI (49.0 mg, 0.255 mmol), HOBt (35.0 mg, 0.255 mmol) and N-methylmorpholine (26.0 mg, 0.255 mmol) in CH2Cl2 (5 mL) was stirred for 20 h (reaction progress monitored by LCMS). The solvent was removed under vacuum, and the residue was purified by preparative HPLC to yield 75 mg of the title compound as a white solid. MS (ES+): m/e 437.1 [M+H]+.

Workup

  1. custom(reaction progress monitored by LCMS)
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-538cd3f3274c49249db503cb0c9e10b6
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

Loading…