Trifluoroacetic acid → 4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]-N,N-dimethyl-benzenesulfonimidamide

HRID 1485648Notes

Reaction equation

HRID 1485648 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9]([O:10][C:11]3[N:44](COCC[Si](C)(C)C)[C:14]4=[N:15][C:16]([C:20]5[CH:25]=[CH:24][C:23]([C:26]6[CH:31]=[CH:30][C:29]([S:32]([N:41]([CH3:43])[CH3:42])(=[O:40])=[N:33]C(=O)C(F)(F)F)=[CH:28][CH:27]=6)=[CH:22][CH:21]=5)=[C:17]([Cl:19])[CH:18]=[C:13]4[N:12]=3)[C@H:5]2[O:4][CH2:3]1.FC(F)(F)C(O)=O>ClCCl>[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9]([O:10][C:11]3[NH:44][C:14]4=[N:15][C:16]([C:20]5[CH:21]=[CH:22][C:23]([C:26]6[CH:27]=[CH:28][C:29]([S:32](=[NH:33])([N:41]([CH3:42])[CH3:43])=[O:40])=[CH:30][CH:31]=6)=[CH:24][CH:25]=5)=[C:17]([Cl:19])[CH:18]=[C:13]4[N:12]=3)[C@H:5]2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736745N-({4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}imidazo[4,5-b]pyridin-5-yl)phenyl]phenyl}(dimethylamino)oxo-lambda6-sulfanylidene)-2,2,2-trifluoroacetamide

Product 1

HCID 1784861274-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]-N,N-dimethyl-benzenesulfonimidamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-({4-[4-(2-{[(3R,3aR,6R,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}imidazo[4,5-b]pyridin-5-yl)phenyl]-phenyl}(dimethylamino)oxo-λ6-sulfanylidene)-2,2,2-trifluoroacetamide (22 mg) and trifluoroacetic acid (0.30 mL) in dichloromethane (1.00 mL) is stirred over night at room temperature. The reaction mixture is concentrated in vacuo and the residue is dissolved in methanol. Aqueous Na2CO3 solution (2 N; 60 μL) is added and the mixture is stirred for 1 h. The reaction mixture is filtered and the crude product is purified by preparative HPLC to give the title compound. LC (method 1): tR=0.86 min; Mass spectrum (ESI+): m/z=556 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in methanol
  3. additionAqueous Na2CO3 solution (2 N; 60 μL) is added
  4. stirringthe mixture is stirred for 1 h
  5. filtrationThe reaction mixture is filtered
  6. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-22fc5e80a5f94d979ea376e2d4cab7d4
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

Loading…