Water → HCID 60204369, compound

HRID 2267314Notes

Reaction equation

HRID 2267314 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:29]=[CH:28][C:9]2[S:10][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][NH:24][C:23]4=[O:27])[N:14]=3)=[CH:12][C:8]=2[CH:7]=1.C(N(CC)CC)C.O>ClCCl>[O:27]=[C:23]1[NH:24][CH2:25][CH2:26][N:22]1[CH2:21][CH2:20][NH:19][C:15]1[N:14]=[C:13]([C:11]2[S:10][C:9]3[CH:28]=[CH:29][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[CH:7][C:8]=3[CH:12]=2)[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 60204332HCID 60204332, compound

Product 1

HCID 60204369HCID 60204369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (61 mg, 0.78 mmol) was added to a mixture of 1-(2-(4-(5-aminobenzo[b]-thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one (230 mg, 0.65 mmol) and triethylamine (131 mg, 1.30 mmol) in dichloromethane (10 mL) at 0° C. and stirred at rt for 6 h. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. After removing the solvent in vacuo the product was purified by column chromatography eluting with methanol/dichloromethane (1:20) to give the title compound as a slightly yellow solid (39 mg, 15%). MS (M+H)+ 397.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×50 mL)
  2. washThe combined organic layer was washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customAfter removing the solvent in vacuo the product
  6. customwas purified by column chromatography
  7. washeluting with methanol/dichloromethane (1:20)

Sources & evidence

ORD record
ord-f7ea7830495543da87c0135c6083265c
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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