Diisopropylethylamine → HCID 59314196, compound

HRID 1047879Notes

Reaction equation

HRID 1047879 reaction equation
[CH:1]1([O:5][C:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([C:21]1([NH2:31])[CH:29](F)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:49][P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:16]([O:18][C:19]([C:21]1([NH:31][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:6]=2[O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[F:49])[CH2:22]1)=[O:20])[CH3:17]

Participants

6

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 593141552-Cyclobutyloxy-3-methylbenzoic acidHCID 68590679HCID 68590679, compound

Product 1

HCID 59314196HCID 59314196, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyclobutoxy-3-methyl-benzoic acid (127 mg, 0.61 mmol), 2-Amino-3-fluoro-indan-2-carboxylic acid ethyl ester (265) (165 mg, 0.74 mmol), HATU 352 mg, 0.93 mmol) in anhydrous DMF (10 mL) is added DIPEA (204 μL, 1.23 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is suspended in H2O (50 mL) and washed with EtOAc (3×50 mL). Organics are combined and washed successively with NaHCO3 and brine, and then the organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-20% EtOAc in heptane) to give a pure product (266) as a colorless oil (210 mg, 84%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. washwashed with EtOAc (3×50 mL)
  3. washwashed successively with NaHCO3 and brine
  4. dry with materialthe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-20% EtOAc in heptane)

Sources & evidence

ORD record
ord-2d5d55d1106b46c09ee11be5b112c730
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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