Tert-Butylamine → HCID 66661260, compound

HRID 408847Notes

Reaction equation

HRID 408847 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([NH:12][C:13](=[O:38])[NH:14][C:15]2[CH:37]=[CH:36][C:18]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[O:29][CH:30]=[C:31]([C:33]([OH:35])=O)[N:32]=4)[CH2:23][CH2:22]3)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10][CH2:9]1.[C:39]([NH2:43])([CH3:42])([CH3:41])[CH3:40].C(N(CC)C(C)C)(C)C>CN(C)C(=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:39]([NH:43][C:33]([C:31]1[N:32]=[C:28]([CH2:27][N:24]2[CH2:25][CH2:26][N:21]([C:19]([C:18]3[CH:36]=[CH:37][C:15]([NH:14][C:13]([NH:12][CH:8]4[CH2:9][CH2:10][CH2:11]4)=[O:38])=[CH:16][CH:17]=3)=[O:20])[CH2:22][CH2:23]2)[O:29][CH:30]=1)=[O:35])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 66661457HCID 66661457, compound

Product 1

HCID 66661260HCID 66661260, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-((4-(4-(3-cyclobutylureido)benzoyl)piperazin-1-yl)methyl)-oxazole-4-carboxylic acid 2,2,2-trifluoroacetate (8 mg, 15 μmol) in N,N-dimethyl-acetamide (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyl uronium hexafluorophosphate (5.7 mg, 154 μmol; HATU), tert-butylamine (1.6 μL, 15 μmol) and N,N-diisopropylethylamine (3.9 μL, 23 μmol). The reaction mixture was stirred at room temperature for 20 hours and was then concentrated under vacuum. The crude residue was purified by acidic reverse phase HPLC to give the title compound (5.6 mg). MS (ESI) m/z 483.1 [M+H]+

Workup

  1. concentrationwas then concentrated under vacuum
  2. customThe crude residue was purified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-f496a1c6cf7d4eb79df1a7993a743240
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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