Diisopropylethylamine → HCID 90204897, compound

HRID 624839Notes

Reaction equation

HRID 624839 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.[CH3:21][NH:22][C:23]([CH3:26])([CH3:25])[CH3:24].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C>CN(C=O)C>[C:23]([N:22]([CH3:21])[C:12]([C:10]1[CH:9]=[CH:8][C:7]([N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[N:11]=1)=[O:14])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 84552N-Methyl-tert-butylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid

Product 1

HCID 90204897HCID 90204897, compoundYield 194%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid (10 mg, 35 μmol), N,2-dimethylpropan-2-amine (CAN 94896-77-2, 3.68 mg, 42.2 μmol), 1-hydroxybenzotriazole hydrate (11 mg, 70 μmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12 mg, 70 μmol) and DIEA (18.2 mg, 24 μl, 141 μmol) in DMF (157 μL) was stirred for 2 d at ambient temperature. The reaction mixture was poured onto ice-water/1N HCl (20 mL), extracted with EtOAc (2×30 mL) and washed with ice-water/brine (20 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give 24 mg of a yellow oil which was purified by TLC (silica gel, Heptane/EtOAc 1:1, elution with DCM/EtOAc 1:1) to give the title compound (11 mg, 89%) as light yellow oil; MS (EI): m/e=354.5 [MH+].

Workup

  1. additionThe reaction mixture was poured onto ice-water/1N HCl (20 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. washwashed with ice-water/brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-942d1415e573497aa4dbf9a0e31a877a
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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