Trifluoroacetic acid → HCID 22280113, compound

HRID 1063756Notes

Reaction equation

HRID 1063756 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[CH:18]=2)=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2.C(O)(C(F)(F)F)=O.[K+].[Br-]>C(#N)C.O>[F:31][C:28]([F:29])([F:30])[C:25]1[CH:26]=[CH:27][C:22]([C:19]2[CH:18]=[C:17]([CH2:16][S:15][C:12]3[CH:13]=[CH:14][C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])=[C:7]4[C:11]=3[CH2:10][CH2:9][CH2:8]4)[O:21][N:20]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 253877Potassium BromideHCID 20827073HCID 20827073, compound

Product 1

HCID 22280113HCID 22280113, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared in the manner analogous to Example 1 using 89A. mp 166-168° C.; HPLC: area %=96.95, r.t.=3.140 min, γ=214 nm, mobile phase=acetonitrile/water w/0.10% TFA. IR (KBr) cm−1: 3140, 3085, 1742, 1322, 1255, 1109; 400 MHz 1H NMR (DMSO-d6): δ 12.96 (br(s), 1H), 7.99 (d, 2H, J=8.3 Hz), 7.81 (d, 2H, J=8.3 Hz), 7.14 (d, 1H, J=8.4 Hz), 6.81 (s, 1H), 6.61 (d, 1H, J=8.4 Hz), 4.63 (s, 2H), 4.23 (s, 2H), 2.76 (t, 4H, J=7.5 Hz), 1.91 (pentet, 2H); MS m/z 450 (M+1). Anal. Calc'd for C22H18F3NO4S: C, 58.79; H, 4.04; N, 3.12. found: C, 58.38; H, 3.92; N, 2.95.

Sources & evidence

ORD record
ord-403f4672dd0747b583815aad2bfe1d4e
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

Loading…