4-Methylmorpholine → HCID 58978202, compound

HRID 1180108Notes

Reaction equation

HRID 1180108 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][N:4]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[C:3]1=[O:18].[CH3:19][CH2:20][N:21]=[C:22]=[N:23][CH2:24][CH2:25][CH2:26][N:27](C)C.[CH:30]1[CH:31]=[CH:32]C2N(O)N=NC=2[CH:35]=1.[CH3:40][N:41]1CCOCC1>CN(C=O)C>[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][N:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:27][C:26]3[CH:35]=[CH:30][C:31]([CH3:32])=[C:24]([NH:23][C:22]4[N:21]=[CH:20][CH:19]=[CH:40][N:41]=4)[CH:25]=3)=[O:15])=[CH:16][CH:17]=2)[C:3]1=[O:18]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58978239HCID 58978239, compound

Product 1

HCID 58978202HCID 58978202, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example H (200 mg, 0.81 mmol) in DMF (10 mL) were added EDCI (200 mg, 1.0 mmol), HOBt (150 mg, 1.5 mmol), NMM (0.5 mL) and Reagent BB (300 mg, 1.5 mmol). After being stirred at RT overnight, the solvent was removed under vacuum. The resulting residue was purified by preparative HPLC to yield pure 4-((3-methyl-2,4-dioxoimidazolidin-1-yl)methyl)-N-(4-methyl-3-(pyrimidin-2-ylamino)phenyl)benzamide (20 mg). 1H NMR (DMSO-d) δ:10.14 (s, 1H), 8.87 (s, 1H),8.35 (d, J=4.8 Hz, 2H), 7.91 (d, J=8 Hz, 2 H), 7.84 (d, J=1.6 Hz, 1H), 7.45 (dd, J=8.4, 2.0 Hz, 1H), 7.41 (d, J=7.7 Hz, 2H), 7.15 (d, J=8.0 Hz, 1H), 6.75 (t, J=4.8 Hz, 1H), 4.56 (s, 2H), 3.89 (s, 2H), 2.87 (s, 3H), 2.15 (s, 3H); MS (ESI) m/e: 431 (M++1).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-085be10aab624bc4948b3d80cbb3d4c1
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

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