Trifluoroacetic acid → Trifluoroacetic acid

HRID 711951Notes

Reaction equation

HRID 711951 reaction equation
[N:1]1([C@@H:6]2[CH2:11][CH2:10][C@H:9]([NH:12]C(=O)OC(C)(C)C)[CH2:8][CH2:7]2)[CH:5]=[N:4][CH:3]=[N:2]1.[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23]>C(Cl)Cl>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[N:1]1([C@@H:6]2[CH2:7][CH2:8][C@H:9]([NH2:12])[CH2:10][CH2:11]2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:22]([OH:24])([C:21]([F:26])([F:25])[F:20])=[O:23]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453987HCID 178453987, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178511582HCID 178511582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (60%, 0.034 g, 0.86 mmol) was added portionwise to a solution of 1H-1,2,4-triazole (0.064 g, 0.92 mmol) in N,N-dimethylformamide (2 mL). After stirred for 5 min, trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl methanesulfonate (0.18 g, 0.61 mmol) was added. The resulting mixture was stirred at 65° C. over weekend. The cooled mixture was poured into ice-cold water, extracted with EtOAc. The organic layers were concentrated and purified on silica gel (eluting with 0 to 5% MeOH in EtOAc) to give tert-butyl [cis-4-(1H-1,2,4-triazol-1-yl)cyclohexyl]carbamate (0.14 g, 86%). LCMS calculated for C13H23N4O2 (M+H)+: m/z=267.2. Found: 267.1. This carbamate intermediate was treated with trifluoroacetic acid (0.28 mL, 3.7 mmol) in methylene chloride (1 mL) at room temperature for 1 h and then concentrated to give the desired product as TFA salt. LCMS calculated for C8H15N4 (M+H)+: m/z=167.1. Found: 167.2.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-9b230fb457b9466aab833ef669238a53
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…