Diisopropylethylamine → HCID 16039649, compound

HRID 1011727Notes

Reaction equation

HRID 1011727 reaction equation
CC[N:3]([CH:7]([CH3:9])C)[CH:4](C)C.[F:10][CH:11]([F:42])[O:12][CH2:13][C@@H:14]([O:16][C:17]1[CH:18]=[C:19]([O:32][C:33]2[N:34]=[CH:35][C:36]([C:39]([OH:41])=O)=[N:37][CH:38]=2)[CH:20]=[C:21]([C:23]([NH:25][C:26]2[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=2)=[O:24])[CH:22]=1)[CH3:15].Cl.N1CCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[N:3]1([C:39]([C:36]2[N:37]=[CH:38][C:33]([O:32][C:19]3[CH:20]=[C:21]([CH:22]=[C:17]([O:16][C@@H:14]([CH3:15])[CH2:13][O:12][CH:11]([F:42])[F:10])[CH:18]=3)[C:23]([NH:25][C:26]3[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=3)=[O:24])=[N:34][CH:35]=2)=[O:41])[CH2:4][CH2:9][CH2:7]1

Participants

7

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 53629642HCID 53629642, compound

Product 1

HCID 16039649HCID 16039649, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (0.41 mL, 2.33 mmol) was added to a mixture of 5-[(3-({(1S)-2-[(difluoromethyl)oxy]-1-methylethyl}oxy)-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylic acid (0.27 g, 0.58 mmol), azetidine hydrochloride (109 mg, 1.17 mmol) and HATU (466 mg, 1.22 mmol) in DMF (5 mL) and stirred at RT for 24 hours. Ethyl acetate (40 mL) was added and the organics washed with water (2×30 mL), brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. The residue was chromatographed on silica, eluting with 0-5% methanol in ethyl acetate, to give the desired compound (124 mg).

Workup

  1. washthe organics washed with water (2×30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. customThe residue was chromatographed on silica
  7. washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-ffe8c9c8fc1549359c0cdc8bf3822780
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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