Formaldehyde → HCID 23130732, compound

HRID 2080218Notes

Reaction equation

HRID 2080218 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1.CC[C@@H]([C@H](NCN[C:36]([O:38][CH2:39]C)=O)C(O)=O)C.C=O.C(OCC)(=O)C>CO>[Cl:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][C:12]1[S:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:23]=[CH:24][C:2]([NH:1][CH2:36][O:38][CH3:39])=[N:3][CH:4]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl Acetate2×HCID 124195N-({[Ethoxy(hydroxy)methylidene]amino}methyl)isoleucineHCID 23130419HCID 23130419, compound

Product 1

HCID 23130732HCID 23130732, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-amino-N-(5-(3-chloro-benzyl)-thiophen-2-ylmethyl)-nicotinamide described in Example A-145 (110 mg, 0.3 mmol) in methanol (10 mL) were added 5,5-dimethylimidazo phospho-2,4-dione (43 mg, 0.33 mmol) and an aqueous solution of 37% formaldehyde (0.5 mL), and the solution was stirred under reflux for 2 hours. NH silica gel was added to the reaction solution, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (65 mg, 0.16 mmol, 54%) was obtained as a slightly yellow solid.

Workup

  1. additionwere added 5,5-dimethylimidazo phospho-2,4-dione (43 mg, 0.33 mmol)
  2. temperatureunder reflux for 2 hours
  3. additionNH silica gel was added to the reaction solution
  4. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-e325a5fc3bdf4d5b8c04ee083e57e2a3
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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