Trifluoroacetic acid → HCID 53259478, compound

HRID 1397885Notes

Reaction equation

HRID 1397885 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:23][C:24](=[O:32])[NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:16][C:17](=[O:22])[NH:18][CH2:19][C:20]#[CH:21])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:23][C:24](=[O:32])[NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:16][C:17](=[O:22])[NH:18][CH2:19][C:20]#[CH:21])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86675735HCID 86675735, compound

Product 1

HCID 53259478HCID 53259478, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

ethyl 2-(3-(1-(4-(tert-butoxycarbonylamino)phenyl)-3-oxo-3-(prop-2-ynylamino)propyl)ureido)acetate (108 mg) was dissolved in 4 ml of DCM and 2 ml of TFA was added then the reaction mixture was let 2 h at room temperature. The mixture was concentrated and the crude was purified on reverse phase (H2O/MeCN) to afford the amine 201 (50 mg, 60%) as a white solid, Rf=0.45 (EtOAc/MeOH 90/10). 1H NMR (200 MHz, DMSO) δ 8.25 (t, J=5.5 Hz, 1H), 6.94 (d, J=8.3 Hz, 2H), 6.56 (d, J=8.5 Hz, 1H), 6.50 (d, J=8.3 Hz, 2H), 6.27 (t, J=6.0 Hz, 1H), 5.05-4.79 (m, 3H), 4.10 (q, J=7.1 Hz, 2H), 3.86-3.71 (m, 4H), 3.14-3.08 (m, 1H), 2.58-2.45 (m, 2H), 1.21 (t, J=7.1 Hz, 3H). HPLC method A tr=5.12 nm (98.1%). ESI-MS m/z: 347.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude was purified on reverse phase (H2O/MeCN)

Sources & evidence

ORD record
ord-8a6e2f1585824040bbdb0f92e18dfaa1
Source dataset
uspto-grants-2014_12
Patent number
US08901295B2

Reaction notes

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