Diisopropylethylamine → HCID 68543486, compound

HRID 1182179Notes

Reaction equation

HRID 1182179 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([S:13]([OH:16])(=[O:15])=O)=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:21][C:22]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:23]=1[C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25].C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([S:13]([NH:21][C:22]3[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:23]=3[C:24]([NH:26][CH:27]([CH3:29])[CH3:28])=[O:25])(=[O:16])=[O:15])=[CH:11][C:10]([C:17]([F:19])([F:20])[F:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167760932-amino-3-methyl-N-(1-methylethyl)benzamide2×HCID 86616009HCID 86616009, compound

Product 1

HCID 68543486HCID 68543486, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2.84 g (10.2 mmol) of 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-sulfonic acid (i.e. the title material from Step C) in 70 mL of dichloromethane was added 1.96 g (10.2 mmol) of 2-amino-3-methyl-N-(1-methylethyl)benzamide (i.e. the title compound of Step E) 1.78 mL (10.2 mmol) of diisopropylethylamine and approximately 5 mg of 4-(dimethylamino)pyridine. The reaction mixture was stirred for 9 hours, then washed with water and dried (sodium sulfate). The solvent was removed with a rotary evaporator. The residue was purified by MPLC (20–40% ethyl acetate in hexanes as eluant) to afford 0.50 g of the title compound as a foamy white solid melting at 69–72° C. 1H NMR (CDCl3) δ 0.1.12 (d, 6H), 2.32 (s, 1H), 3.85 (m, 1H), 5.96 (brd, 1H), 7.07 (s, 1H), 7.35 (m, 3H), 7.39 (dd, 1H), 7.89 (dd, 1H), 8.20 (dd, 1H), 9.26 (s, 1H).

Workup

  1. washwashed with water
  2. dry with materialdried (sodium sulfate)
  3. customThe solvent was removed with a rotary evaporator
  4. customThe residue was purified by MPLC (20–40% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-242ce80f00e748b192c097b855b56771
Source dataset
uspto-grants-2007_10
Patent number
US07288554B2

Reaction notes

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