Morpholine → HCID 60204420, compound

HRID 2267329Notes

Reaction equation

HRID 2267329 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl.O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

8

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 57428829HCID 57428829, compound

Product 1

HCID 60204420HCID 60204420, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(2-(methylthio)pyrimidin-4-yl)thiophene-2-carboxylic acid (200 mg, 0.79 mmol), morpholine (69 mg, 0.79 mmol), EDCI (182 mg, 0.95 mmol), HOAt (21 mg, 0.16 mmol) and triethylamine (159 mg, 1.58 mmol) in dichloromethane (20 mL) was stirred at rt for 24 h. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue purified by flash chromatography eluting with ethyl acetate/hexane (1:1) to give the intermediate (5-(2-(methylthio)pyrimidin-4-yl)thiophen-2-yl)(morpholino)methanone as a white solid (200 mg, 78%). MS (M+H)+ 322.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×50 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-f707f6aef0d640f99d7b20a1efd848b5
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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