Trifluoroacetic acid → HCID 54597015, compound

HRID 1853136Notes

Reaction equation

HRID 1853136 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:21]2[N:25](C(OC(C)(C)C)=O)[C:24]3[CH:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:23]=3[N:22]=2)=[N:11][C:12]([NH:15][C:16](=[O:20])[CH2:17][C:18]#[N:19])=[CH:13][N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:20])[CH2:17][C:18]#[N:19])=[N:11][C:10]=1[C:21]1[NH:25][C:24]2[CH:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:23]=2[N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58084346HCID 58084346, compound

Product 1

HCID 54597015HCID 54597015, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(2-cyanoethanamido)pyrazin-2-yl)-6-methyl-1H-benzo[d]imidazole-1-carboxylate (isolated from Step 2) was dissolved in DCM (5 mL) and TFA (28.29 mg, 19.11 μL, 0.2481 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as a yellow solid (8 mg, 10.5% Yield). 1H NMR (400.0 MHz, CDCl3) δ 2.4 (3H, s), 3.95 (2H, s), 7.15 (1H, d), 7.42-7.49 (1H, m), 7.52-7.58 (1H, m), 8.0 (1H, br s), 8.62 (1H, s), 10.55 (1H, s), 12.8 (1H, vbr s); MS (ES+) 308.0.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

Sources & evidence

ORD record
ord-8b1ce075bb004d5ab44a5ef4df7e0655
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

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