Diisopropylethylamine → (S)-2-(2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide

HRID 1471659Notes

Reaction equation

HRID 1471659 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]([O:12]C)=O)[N:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)[CH:2]=[CH2:3].[NH2:18][C@@H:19]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=1)[C:20]([N:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH3:23])=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]([NH:18][C@@H:19]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=2)[C:20]([N:22]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[CH3:23])=[O:21])=[O:12])[N:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)[CH:2]=[CH2:3]

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 90280507(S)-2-amino-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamideHCID 90281162methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 90281299(S)-2-(2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamideYield 24.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (110 mg, 0.48 mmol) and (S)-2-amino-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide (194 mg, 0.48 mmol) in DMF (2 mL) was added HATU (228 mg, 0.6 mmol) and DIEA (193 mg, 1.5 mmol). Upon completion of the reaction, the product was purified by reverse phase HPLC eluting with acetonitrile/water (with 0.1% TFA) to afford (S)-2-(2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-3-(3-bromophenyl)-N-(4-chlorophenyl)-N-methylpropanamide (68 mg, 24%) as a solid. MS (m/z): 582.9 [M+H]+; HPLC retention time 4.52 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. customUpon completion of the reaction
  2. customthe product was purified by reverse phase HPLC
  3. washeluting with acetonitrile/water (with 0.1% TFA)

Sources & evidence

ORD record
ord-bd3bdf3a997d421aa75474e1d8a6268c
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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