Diisopropylethylamine → HCID 67496190, compound

HRID 1628290Notes

Reaction equation

HRID 1628290 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[C:22]([O:26][C:27]([C@@H:29]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=1[Cl:41])[C:30](O)=[O:31])=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C)C=O>[C:22]([O:26][C:27]([C@@H:29]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=1[Cl:41])[C:30]([NH:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[O:31])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67497383HCID 67497383, compoundHCID 67498105HCID 67498105, compound

Product 1

HCID 67496190HCID 67496190, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 3-amino-5-(2-methylpyridin-4-yl)benzoate (100 mg, 0.35 mmol), (S)-2-(tert-butoxycarbonyl)-3-(2,4-dichlorophenyl)-propanoic acid (152 mg, 0.45 mmol), HBTU (174 mg, 0.45 mmol) and N-ethyl-N-isopropylpropan-2-amine (92 μl, 0.53 mmol) in N,N-dimethylformamide (0.70 mL) was allowed to stir at 80° C. for 4 hours. Upon completion, the mixture was directly purified by HPLC to give 206 mg of tert-butyl 3-((S)-2-(tert-butoxycarbonyl)-3-(2,4-dichlorophenyl)propanamido)-5-(2-methylpyridin-4-yl)benzoate 49.1C. LCMS (ES+) m/z 601.

Workup

  1. customUpon completion, the mixture was directly purified by HPLC

Sources & evidence

ORD record
ord-516cb67e0ddb41bb8a03653cc1d8445b
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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