Hydrochloric Acid → HCID 60090595, compound

HRID 351615Notes

Reaction equation

HRID 351615 reaction equation
[OH:1][CH2:2][CH:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18](=O)[C:19]([CH3:24])=[CH:20]N(C)C)[CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:26]1([NH:29][C:30]([NH2:32])=[NH:31])[CH2:28][CH2:27]1.Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[C:19]([CH3:24])=[CH:20][N:32]=[C:30]([NH:29][CH:26]3[CH2:28][CH2:27]3)[N:31]=2)[CH:17]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 73701889HCID 73701889, compoundHCID 178512453HCID 178512453, compound

Product 1

HCID 60090595HCID 60090595, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(3-Dimethylamino-2-methyl-acryloyl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-phenyl-ethyl)-amide (100 mg, 0.29 mmol) was combined with cyclopropyl guanidine.HCl (80 mg) and potassium carbonate (121 mg) in N,N-dimethylacetamide (2 mL). The resulting suspension was heated and stirred at 100° C. for 24 hours. The crude material was diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried over MgSO4 then concentrated in vacuo. Purification by preparative TLC (silica, 1:1 EtOAc:Hexanes) afforded III-a-162 as a yellow solid (7.8 mg). HPLC Method B, Rt=4.29 minutes; LC/MS(m/z) 378.2 (M+1), 376.2 (M−1); 1H NMR consistent with structure.

Workup

  1. temperatureThe resulting suspension was heated
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationthen concentrated in vacuo
  5. customPurification by preparative TLC (silica, 1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-12e1e83987b24a3ba56648032ba4b395
Source dataset
uspto-grants-2004_06
Patent number
US06743791B2

Reaction notes

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