Diisopropylethylamine → HCID 68310218, compound

HRID 1480800Notes

Reaction equation

HRID 1480800 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][C:27]=1[O:35][CH3:36].Cl.[CH3:38][O:39][CH:40]1[CH2:43][NH:42][CH2:41]1.CCN(C(C)C)C(C)C>C1COCC1>[NH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([N:42]2[CH2:43][CH:40]([O:39][CH3:38])[CH2:41]2)=[O:32])=[CH:28][C:27]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2880572486-69-3HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222428583-Methoxyazetidine hydrochloride

Product 1

HCID 68310218HCID 68310218, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HATU (2.70 g, 7.10 mmol) was added to a solution of 4-amino-3-methoxybenzoic acid (880 mg, 5.26 mmol), 3-methoxyazetidine hydrochloride (0.971 g, 7.86 mmol) and DIPEA (2.85 mL, 16.32 mmol) in THF (15 mL) at room temperature. THF was removed under reduced pressure, and the residue partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 100% EtOAc in cyclohexane followed by a second chromatography eluting with 0 to 4% MeOH in DCM to afford the title compound (728 mg, 59%).

Workup

  1. customTHF was removed under reduced pressure
  2. customthe residue partitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 0 to 100% EtOAc in cyclohexane
  9. washeluting with 0 to 4% MeOH in DCM

Sources & evidence

ORD record
ord-280f5d27610f4ad9a4707e7745759e20
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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