1,1,3,3-Tetramethylguanidine → HCID 60026711, compound

HRID 400666Notes

Reaction equation

HRID 400666 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:39])([CH3:38])[CH2:12][C:13]([OH:37])([C:33]([F:36])([F:35])[F:34])[CH2:14][C:15]#[C:16][C:17]2[C:22]([NH:23]C(=O)C(F)(F)F)=[CH:21][N:20]=[C:19]([CH:30]([CH3:32])[CH3:31])[N:18]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.CN(C)C(=N)N(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:38])([CH3:39])[CH2:12][C:13]([CH2:14][C:15]2[NH:23][C:22]3[CH:21]=[N:20][C:19]([CH:30]([CH3:32])[CH3:31])=[N:18][C:17]=3[CH:16]=2)([OH:37])[C:33]([F:36])([F:35])[F:34])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 664601,1,3,3-TetramethylguanidineHCID 86600088HCID 86600088, compound

Product 1

HCID 60026711HCID 60026711, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-{4-[6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-2-isopropylpyrimidin-5-yl}-2,2,2-trifluoroacetamide (58 mg, 0.1 mmol) in 1 mL of anhydrous dioxane was added tetramethylguanidine (0.05 mL, 0.4 mmol) and the reaction mixture stirred and heated in oil bath maintained at 100° C. for 1 hour. Purification by preparative TLC over silica gel eluting with 5% methanol in dichloromethane provided the title compound as a light cream colored solid, (25 mg, 52% yield) M+H=482.

Workup

  1. temperatureheated in oil bath
  2. customPurification by preparative TLC over silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7e15258e0bed4b34831279933d096995
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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