Trifluoroacetic acid → HCID 91407828, compound

HRID 393831Notes

Reaction equation

HRID 393831 reaction equation
[C:1]1([S:7]([NH:10][NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH:21]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[OH:22])=[CH:15][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>CC#N.O>[C:1]1([S:7]([NH:10][NH:11][C:12](=[O:29])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH:21]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[OH:22])=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 91374349HCID 91374349, compound

Product 1

HCID 91407828HCID 91407828, compound

Reagents, catalysts & solvents 1

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

Procedure

Example 36 was synthesized in accordance with the methods of Example 33, except that 4-(3-cyclohexyl-3-hydroxy-1-propynyl)-benzoic acid, 2-(phenylsulfonyl)hydrazide (Example 35) was used instead of 4phenacetylenyl-benzoic acid, 2-(phenylsulfonyl)hydrazide. MS: 403 (M+1 for C21H26N2O4S1); mp 158-159° C.; TLC (SiO2) Rf=0.3 (50% EtOAc/hexanes); HPLC (C18 column, 7:3 CH3CN/H2O+0.1%TFA) 95%, RT=5.0 min. 1H NMR (DMSO-d6) δ 1.10-1.65 (m, 12H), 2.46-2.61 (m, 2H), 4.00 (s, 1H), 7.20 (d, 2 H, J=8.1 Hz), 7.46-7.57 (m, 5H), 7.78 (d, 2H, J=7.3 Hz), 9.93 (s, 1H, 10.56 (s, 1H).

Sources & evidence

ORD record
ord-bc50ffe3f2734f6a92898509587c555f
Source dataset
uspto-grants-2004_10
Patent number
US06809119B2

Reaction notes

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