Trifluoroacetic acid → Benzimidazole

HRID 1619791Notes

Reaction equation

HRID 1619791 reaction equation
FC(F)[C:3]1[N:7](C2N=C(N3CCOCC3)N=C(OC3CCN(C(OC(C)(C)C)=O)CC3)N=2)[C:6]2[CH:34]=[CH:35][CH:36]=[C:37](OC)[C:5]=2[N:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:4]1[C:5]2[CH:37]=[CH:36][CH:35]=[CH:34][C:6]=2[N:7]=[CH:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66698089HCID 66698089, compound

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treatment of tert-butyl 4-(4-(2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl)-6-morpholino-1,3,5-triazin-2-yloxy)piperidine-1-carboxylate (112 mg, 0.2 mmol) with TFA (5 mL) in CH2Cl2 (10 mL), followed by quenching with aqueous NH3 gave 2-(difluoromethyl)-4-methoxy-1-(4-morpholinyl)-6-(4-piperidinyloxy)-1,3,5-triazin-2-yl]-1H-benzimidazole: 1H NMR (DMSO-d6) δ 7.96 (dd, J=8.4, 0.5 Hz, 1H), 7.71 (t, JHF=52.8 Hz, 1H), 7.44 (t, J=8.3 Hz, 1H), 6.98 (d, J=7.7 Hz, 1H), 5.11 (m, 1H), 3.98 (s, 3H), 3.83 (m, 4H), 3.71 (m, 4H), 3.00 (m, 2H), 2.62 (m, 2H), 2.00 (m, 2H), 1.58 (m, 2H).

Workup

  1. customby quenching with aqueous NH3

Sources & evidence

ORD record
ord-fa85fb6ea8064ca596c8fdbadf2f6623
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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