Tert-Butylamine → N-(2-tert-Butylcarbamoyl-ethyl)-N-isopropyl-3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

HRID 2268687Notes

Reaction equation

HRID 2268687 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]([N:11]([C:17](=[O:35])[C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][NH:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[CH:21]=[C:20]([CH3:34])[CH:19]=1)[CH2:12][CH2:13][C:14](O)=[O:15])([CH3:10])[CH3:9].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:69]([NH2:73])([CH3:72])([CH3:71])[CH3:70]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:69]([NH:73][C:14]([CH2:13][CH2:12][N:11]([CH:8]([CH3:9])[CH3:10])[C:17](=[O:35])[C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][NH:27][C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)[CH:21]=[C:20]([CH3:34])[CH:19]=1)=[O:15])([CH3:72])([CH3:71])[CH3:70]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 699505203-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid trifluoroacetate

Product 1

HCID 18349007N-(2-tert-Butylcarbamoyl-ethyl)-N-isopropyl-3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-(isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid trifluoroacetate (0.018 g) and PyBroP® (0.017 g) in DMF (1 ml) was added DIPEA (0.012 ml) followed by tert-butylamine (0.005 ml), after 1 min. The reaction mixture was stirred at room temperature for 18 h, and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.009 g) was obtained as a colourless oil by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a60d6eef46df4b5db48e25393b485f13
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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