Trifluoroacetic acid → HCID 71546517, compound

HRID 1403701Notes

Reaction equation

HRID 1403701 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28](=[O:29])[C:20]=2[C:19]2[C:14](=[CH:15][C:16]([NH:30][C:31](=[O:37])[CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:17][CH:18]=2)[C:13]1=[O:38])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28](=[O:29])[C:20]=2[C:19]2[C:14](=[CH:15][C:16]([NH:30][C:31](=[O:37])[CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:17][CH:18]=2)[C:13]1=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71546350HCID 71546350, compound

Product 1

HCID 71546517HCID 71546517, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 18 (0.080 g, 0.145 mmol) was treated with TFA (0.5 mL) in chloroform (5 mL) for 2 h at room temperature. The solvent was removed on a rotary evaporator and the residue was then basified with 2 N NH3 in methanol to get the free amine, which was purified by silica gel column chromatography, eluting with chloroform-methanol, 8.8:1.2, to yield the product 23 (0.040 g, 62%) as a brown solid: mp 225-227° C. IR (KBr) 3067, 1739, 1673, 1574, 1535, 1511, 1202, 1134, 722 cm−1; 1H NMR (CD3OD, 300 MHz) 8.52 (d, J=2.1 Hz, 1H), 8.29 (d, J=6.8 Hz, 1H), 7.43 (m, 5H), 4.50 (t, J=2.1 Hz, 2H), 3.78 (s, 3H), 3.10 (m, 2H), 2.22 (m, 2H); 13C NMR (CD3OD, 125 MHz) δ 191.6, 169.9, 166.8, 164.9, 155.4, 138.8, 137.9, 135.7, 134.9, 132.2, 129.6, 127.2, 125.0, 124.8, 124.1, 123.9, 118.6, 109.6, 52.9, 42.5, 38.2, 28.6; ESIMS m/z (relative intensity) 420 (MH+, 100); HRESIMS calcd for C23H21N3O5 420.1559 (MH+), found 420.1554 (MH+); HPLC purity: 100% (1% TFA in MeOH—H2O, 50:50).

Workup

  1. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-a4b8c557849545239983fd8937d3f0b9
Source dataset
uspto-grants-2014_12
Patent number
US08912213B2

Reaction notes

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