Tert-Butylamine → HCID 18348959, compound

HRID 2268688Notes

Reaction equation

HRID 2268688 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:26]=[C:27]([O:29][CH2:30][CH2:31][NH:32][C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[CH:28]=1)[C:12]([N:14]([CH:23]([CH3:25])[CH3:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])=[O:13].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:72]([NH2:76])([CH3:75])([CH3:74])[CH3:73]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:72]([NH:76][C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH:23]([CH3:25])[CH3:24])[C:12](=[O:13])[C:11]1[CH:26]=[C:27]([O:29][CH2:30][CH2:31][NH:32][C:33]2[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=2)[CH:28]=[C:9]([Cl:8])[CH:10]=1)=[O:21])([CH3:75])([CH3:74])[CH3:73]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 69948305HCID 69948305, compound

Product 1

HCID 18348959HCID 18348959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-({3-chloro-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-isopropyl-amino)-hexanoic acid trifluoroacetate (0.02 g) and PyBroP® (0.021 g) in DMF (1 ml) was added DIPEA (0.016 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 (0.0094 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-6b22db40860940c1a4460824e51f2cc4
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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