Pivaloyl chloride → (8aS)-7-(2,2-Dimethylpropyl)-2-[(1S,2R)-2-phenylcyclopropyl]tetrahydro imidazo[1,5-a]pyrazine-1,3(2H,5H)-dione

HRID 1260480Notes

Reaction equation

ClC1C(Cl)=CC=CC=1N[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18](=[O:31])[N:19]([C@H:22]3[CH2:24][C@@H:23]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:21])[C@@H:14]2[CH2:13]1)=O.Cl.[C:33]1([C@H:39]2C[C@@H]2N2C(=O)[C@@H]3CNCCN3C2=O)[CH:38]=CC=C[CH:34]=1.C(Cl)(=O)C(C)(C)C>C(Cl)Cl>[CH3:34][C:33]([CH3:39])([CH3:38])[CH2:10][N:12]1[CH2:17][CH2:16][N:15]2[C:18](=[O:31])[N:19]([C@H:22]3[CH2:24][C@@H:23]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:21])[C@@H:14]2[CH2:13]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of Example 4, D2 (1 eq) and TEA (1.1 eq) in DCM (0.08M) was added pivaloyl chloride (2.1 eq) and the reaction mixture was stirred at 25° C. for 2 h. The crude product was purified by preparative RP-HPLC using H2O (0.1% TFA) and MeCN (0.1% TFA) as eluents, affording the title compound. 1H NMR (400 MHz, DMSO-d6, 300K) 7.48-7.18 (5H, m), 4.75-4.63 (1H, m), 4.42-4.33 (1H, m), 4.05-3.93 (2H, m), 3.15-2.80 (3H, m), 2.72-2.63 (1H, m), 2.50-2.38 (1H, m), 1.58-1.51 (1H, m), 1.48-1.38 (1H, m), 1.35 (9H, s). MS (ES) C20H25N3O3 requires: 354 found: 355 (M+H)+.

Workup

customThe crude product was purified by preparative RP-HPLC

Sources & evidence

ORD record: ord-f65c2b12be854e9a858e2c09426f0ba0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470823B2

Reaction notes

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