Trifluoroacetic acid → HCID 90067364, compound

HRID 929215Notes

Reaction equation

HRID 929215 reaction equation
C(O)(C(F)(F)F)=O.[C:8]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]3[N:20]=[C:21]([NH:31][CH:32]4[CH2:36][O:35][C@@H:34]5[C@H:37]([O:40][Si](C(C)(C)C)(C)C)[CH2:38][O:39][C@H:33]45)[N:22](COCC[Si](C)(C)C)[C:17]3=[CH:16][C:15]=2[Cl:48])=[CH:10][CH:9]=1>C(Cl)Cl>[C:8]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]3[N:20]=[C:21]([NH:31][CH:32]4[C@H:33]5[O:39][CH2:38][C@@H:37]([OH:40])[C@H:34]5[O:35][CH2:36]4)[NH:22][C:17]3=[CH:16][C:15]=2[Cl:48])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90042513HCID 90042513, compound

Product 1

HCID 90067364HCID 90067364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step B(b): TFA (0.1 mL) was added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-N-((3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-amine (major isomer) (20 mg, 0.029 mmol) in DCM (0.5 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.1% TFA to give the title compound. LC-MS: calculated for C24H21ClN4O3 448.13 observed m/e: 449.15 (M+H)+ (Rt 1.18/2 min); 1H NMR δ (ppm) (CD3OD): 7.88-7.34 (m, 10H), 4.75 (m, 1H), 4.62 (m, 1H), 4.46 (m 1H), 4.37 (m, 1H), 4.28 (dd, 1H), 4.00 (dd, 1H), 3.81 (dd, 1H), 3.68 (dd, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  3. washeluting with acetonitrile/water+0.1% TFA

Sources & evidence

ORD record
ord-d784138049824fe9b0ae403f7b41caef
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

Loading…