Diisopropylethylamine → HCID 59149726, compound

HRID 1675166Notes

Reaction equation

HRID 1675166 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1([C:30]2[CH:40]=[CH:39][C:33]([O:34][CH2:35][C:36](O)=[O:37])=[CH:32][CH:31]=2)[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=3)[N:22]=2)[CH2:13][CH2:12]1.[CH3:41][O:42][CH2:43][CH2:44][NH:45][CH3:46].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[OH:10][C:11]1([C:30]2[CH:40]=[CH:39][C:33]([O:34][CH2:35][C:36]([N:45]([CH2:44][CH2:43][O:42][CH3:41])[CH3:46])=[O:37])=[CH:32][CH:31]=2)[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([C:23]([C:26]([F:28])([F:27])[F:29])=[N:24][N:25]=3)[N:22]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67339395HCID 67339395, compound

Product 1

HCID 59149726HCID 59149726, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

DIPEA (0.321 mL, 1.94 mmol) was added to 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]acetic acid (283 mg, 0.65 mmol), N-(2-methoxyethyl)methylamine (63 mg, 0.71 mmol) and HATU (270 mg, 0.71 mmol) in DMF (5 mL) at 20° C. under nitrogen. The resulting solution was stirred at 20° C. for 4 hours. Water (50 mL) was then added and the mixture was extracted with DCM (2×50 mL). The combined organics were dried (Na2SO4), filtered and evaporated to give a orange oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane then 0 to 10% MeOH in EtOAc. Pure fractions were evaporated to dryness then tritutated with isohexane, filtered and dried to afford 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]-N-(2-methoxyethyl)-N-methylacetamide (161 mg, 48.9%) as a white solid.

Workup

  1. extractionthe mixture was extracted with DCM (2×50 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give a orange oil
  6. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane
  7. customPure fractions were evaporated to dryness
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-fcef7b7136334532a091500ec8e33474
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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