Acetic Anhydride → (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-acetamido-N-(4-(4-fluorophenoxy)phenyl)pentanamide

HRID 1630289Notes

Reaction equation

HRID 1630289 reaction equation
CCN(C(C)C)C(C)C.[C:10](OC(=O)C)(=[O:12])[CH3:11].[N:17]1([CH2:22][C:23]([NH:25][C@@H:26]([CH2:44][CH2:45][CH2:46][NH2:47])[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])=[O:24])[CH:21]=[N:20][CH:19]=[N:18]1>C1COCC1>[N:17]1([CH2:22][C:23]([NH:25][C@@H:26]([CH2:44][CH2:45][CH2:46][NH:47][C:10](=[O:12])[CH3:11])[C:27]([NH:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:34][CH:35]=2)=[O:28])=[O:24])[CH:21]=[N:20][CH:19]=[N:18]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 67010500(S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamide

Product 1

HCID 67009537(S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-acetamido-N-(4-(4-fluorophenoxy)phenyl)pentanamideYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step (b) DIEA (0.10 mL, 0.57 mmol) and acetic anhydride (0.025 mL, 0.27 mmol) was added to (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamide (115 mg, 0.269 mmol) in THF (5 mL). The reaction mixture was stirred for 2 hours and then concentrated. Product was purified from the residue by reverse phase HPLC to give Compound 254, (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-acetamido-N-(4-(4-fluorophenoxy)phenyl)pentanamide (34 mg, 0.073 mmol, 27%) as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): 10.21 (s, 1H), 8.75-8.73 (m, 1H), 8.47 (s, 1H), 7.85-7.82 (m, 1H), 7.63-7.58 (m, 2H), 7.24-7.18 (m, 2H), 7.04-6.92 (m, 4H), 4.99 (s, 2H), 4.46-4.38 (m, 1H), 3.12-3.01 (m, 2H), 1.80 (s, 3H), 1.79-1.37 (m, 4H). MS (EI) for C23H25FN6O4. found 469.1 (MH+).

Workup

  1. concentrationconcentrated
  2. customProduct was purified from the residue by reverse phase HPLC

Sources & evidence

ORD record
ord-ed4f9adbe98b46c4a8879510d40eb2c9
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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