Dimethylformamide → HCID 17989425, compound

HRID 1353062Notes

Reaction equation

HRID 1353062 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][C:29]4[CH:34]=CC=CC=4)[CH:24]=3)[C:19]2=[O:35])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH:36]1(N=C=N)[CH2:41]CCC[CH2:37]1.CN(C=O)C>ClCCl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH2:29][CH:34]=[C:36]([CH3:41])[CH3:37])[CH:24]=3)[C:19]2=[O:35])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12048208N-CyclohexylcarbodiimideHCID 17989398HCID 17989398, compound

Product 1

HCID 17989425HCID 17989425, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of this acid (67 mg, 0.27 mmol), 3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine [Example A4] (67 mg, 0.28 mmol) and N-cyclohexylcarbodiimide resin (1.69 mol. eq./g, 0.46 g, 0.78 mmol) was stirred in a 50:50 mixture of DMF and dichloromethane (1.5 ml) at room temperature under argon for 16 h. The mixture was filtered through filter-aid and the resin washed several times with dichloromethane. The filtrate was evaporated and the crude residue purified by flash chromatography on silica gel eluting with methanol in dichloromethane to yield the title compound as a brown oil;

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthrough filter-aid
  3. washthe resin washed several times with dichloromethane
  4. customThe filtrate was evaporated
  5. customthe crude residue purified by flash chromatography on silica gel eluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-87c2343912e64a2f87b4f01d7dca5560
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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