Diisopropylethylamine → HCID 16039604, compound

HRID 1175883Notes

Reaction equation

HRID 1175883 reaction equation
CN(C(ON1N=NC2C=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C@H:26]([O:29][C:30]1[CH:31]=[C:32]([O:45][C:46]2[N:47]=[CH:48][C:49]([C:52]([OH:54])=O)=[N:50][CH:51]=2)[CH:33]=[C:34]([C:36]([NH:38][C:39]2[CH:43]=[CH:42][N:41]([CH3:44])[N:40]=2)=[O:37])[CH:35]=1)[CH2:27][CH3:28].Cl.N1CCC1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C.CCOCC>[N:15]1([C:52]([C:49]2[N:50]=[CH:51][C:46]([O:45][C:32]3[CH:33]=[C:34]([CH:35]=[C:30]([O:29][C@@H:26]([CH3:25])[CH2:27][CH3:28])[CH:31]=3)[C:36]([NH:38][C:39]3[CH:43]=[CH:42][N:41]([CH3:44])[N:40]=3)=[O:37])=[N:47][CH:48]=2)=[O:54])[CH2:14][CH2:13][CH2:10]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12308726Azetidine hydrochlorideHCID 53629638HCID 53629638, compound

Product 1

HCID 16039604HCID 16039604, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

HATU (34 mg, 0.89 mmol) was added to 5-[(3-{[(1S)-1-methylpropyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylic acid (190 mg, 0.4 mmol) and azetidine hydrochloride (84 mg, 0.89 mmol) in DMF (5 mL). DIPEA (0.311 mL, 1.79 mmol) was added and the reaction was stirred for 16 hours. The reaction mixture was added to ethyl acetate (20 mL), washed with water (10 mL), 2N citric acid (10 mL), saturated aqueous sodium hydrogencarbonate (10 mL) and brine (10 mL), then dried (MgSO4), filtered and evaporated under reduced pressure to a gummy residue. The residue was purified by chromatography on silica, eluting with 50-100% ethyl acetate in hexane, to give a gum which was taken up in 50% ethyl acetate in ether and washed twice with water, brine (10 mL) then dried (MgSO4) to give the desired product as a foam (58 mg).

Workup

  1. washwashed with water (10 mL), 2N citric acid (10 mL), saturated aqueous sodium hydrogencarbonate (10 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure to a gummy residue
  5. customThe residue was purified by chromatography on silica
  6. washeluting with 50-100% ethyl acetate in hexane
  7. customto give a gum which
  8. washwashed twice with water, brine (10 mL)
  9. dry with materialthen dried (MgSO4)

Sources & evidence

ORD record
ord-84554c20dbd84cbcb00f3e107b1f959c
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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