Trifluoroacetic acid → HCID 90067364, compound

HRID 929214Notes

Reaction equation

HRID 929214 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

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 (minor isomer) (3.2 mg, 4.61 μmol) in DCM (0.5 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.1% TFA, to give title compound. LC-MS: calculated for C24H21ClN4O3 448.13 observed m/e: 449.16 (M+H)+ (Rt 1.10/2 min); 1H NMR δ (ppm) (CD3OD): 7.72 (m, 5H), 7.61 (m, 1H), 7.49 (m, 3H), 7.54 (m, 1H), 4.61 (m, 3H), 4.31 (m, 1H), 4.14 (m, 1H), 4.03 (d, 1H), 3.91 (dd, 1H), 3.62 (dd, 1H).

Workup

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

Sources & evidence

ORD record
ord-a85d7080e38c472eb5b988b3e7e6d5ce
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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