Diisopropylethylamine → HCID 86707802, compound

HRID 2174395Notes

Reaction equation

HRID 2174395 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([OH:8])=O)(=[O:4])=[O:3].[F:9][C:10]1([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH2:25][C:24]([C:30]4[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=4)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=3)=[CH:17][CH:16]=2)[CH2:13][CH:12]([NH2:14])[CH2:11]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:9][C:10]1([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH2:25][C:24]([C:30]4[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=4)([C:26]([F:27])([F:28])[F:29])[O:23][N:22]=3)=[CH:19][CH:20]=2)[CH2:13][CH:12]([NH:14][C:6](=[O:8])[CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:11]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 37328412-Methanesulfonylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86707800HCID 86707800, compound

Product 1

HCID 86707802HCID 86707802, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(methylsulfonyl)acetic acid (22 mg, 0.16 mmol) was added to 3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)cyclobutanamine (Preparation 16, 50.0 mg, 0.10 mmol) in DMF (1.5 mL) along with DIPEA (54 μL, 0.31 mmol) and HATU (61 mg, 0.16 mmol). The mixture is stirred for 3 days at room temperature. The reaction mixture is partitioned between brine (5 mL) and EtOAc (5 mL). The organics are separated, dried over MgSO4, filtered and evaporated to give a residue, which is purified on regular silica eluting from neat DCM to 15% MeOH/DCM to give the title compound (20 mg): 1H NMR (DMSO-d6) δ: 8.83 (1H, d), 7.85 (2H, s), 7.79 (2H, d), 7.58 (2H, d), 4.60-4.51 (1H, m), 4.42-4.30 (2H, m), 4.04 (2H, s), 3.12 (3H, s), 2.96-2.86 (2H, m), 2.65-2.54 (2H, m); m/z (Cl) 602.

Workup

  1. customThe reaction mixture is partitioned between brine (5 mL) and EtOAc (5 mL)
  2. customThe organics are separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a residue, which
  7. customis purified on regular silica eluting from neat DCM to 15% MeOH/DCM

Sources & evidence

ORD record
ord-03c561c10660492fa3dc891fb752a3f0
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

Loading…