Trifluoroacetic acid → HCID 57936034, compound

HRID 1434632Notes

Reaction equation

HRID 1434632 reaction equation
[NH2:1][C@H:2]([CH:20]([CH3:22])[CH3:21])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:7]([CH3:19])([CH3:18])[CH2:6]1)=[O:4].C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[N:39]([CH:42]([CH3:44])[CH3:43])=[C:40]=[O:41]>C(Cl)Cl>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C@H:2]([NH:1][C:40]([NH:39][CH:42]([CH3:44])[CH3:43])=[O:41])[CH:20]([CH3:22])[CH3:21])[CH2:6][C:7]2([CH3:18])[CH3:19])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 57936049HCID 57936049, compound

Product 1

HCID 57936034HCID 57936034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-amino-1-(4-(4-chlorophenyl)-3,3-dimethylpiperazin-1-yl)-3-methylbutan-1-one, TFA (30 mg, 0.07 mmol) and DIPEA (0.14 mmol) in CH2Cl2 (1 mL), was added 2-isocyanatopropane (7.00 mg, 0.08 mmol). The mixture was stirred at rt for 2 h and concentrated. The residue was purified by preparative HPLC to afford (R)-1-(1-(4-(4-chlorophenyl)-3,3-dimethylpiperazin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-isopropylurea (11 mg, TFA salt) as a white solid. MS found 409.15 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-02fc842477694aeca956641325dff5a0
Source dataset
uspto-grants-2009_11
Patent number
US07615556B2

Reaction notes

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