Hydrochloric Acid → HCID 25026510, compound

HRID 871916Notes

Reaction equation

Cl.[CH3:2][S:3]([C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][C:12]2[N:16]=[C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[O:14][N:13]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(OC(N1[CH2:37][CH2:36][CH:35]([C:38]2O[N:41]=[C:40](COC3C=CC(S(C)(=O)=O)=CC=3)[N:39]=2)[CH2:34]C1)=O)(C)(C)C.CCN(C(C)C)C(C)C.ClC1N=CC(CC)=CN=1>CC(O)C>[CH2:36]([C:35]1[CH:38]=[N:39][C:40]([N:20]2[CH2:21][CH2:22][CH:17]([C:15]3[O:14][N:13]=[C:12]([CH2:11][O:10][C:9]4[CH:8]=[CH:7][C:6]([S:3]([CH3:2])(=[O:5])=[O:4])=[CH:24][CH:23]=4)[N:16]=3)[CH2:18][CH2:19]2)=[N:41][CH:34]=1)[CH3:37]

Participants

Conditions

Temperature: 70 °C

Procedure

To the crude HCl salt (0.18 g, ˜0.5 mmol) of 4-[3-(4-methanesulfonyl-phenoxymethyl)-[1,2,4]oxadiazol-5-yl]-piperidine, prepared by treatment of 4-[3-(4-methanesulfonyl-phenoxymethyl)-[1,2,4]oxadiazol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 81) in dixoane with 4N HCl, was added 2-propanol (3 mL), followed by DIPEA (0.13 g, 1 mmol) and 2-Chloro-5-ethyl-pyrimidine (0.14 g, 1 mmol). The resulting mixture was stirred at 70° C. overnight. After concentration in vacuo, the residue was purified by silica column chromatography with EtOAc/hexanes to afford the desired product. 1H NMR (CDCl3): δ 8.18 (2H, s), 7.89 (2H, d, J=8.8 Hz), 7.15 (2H, d, J=8.8 Hz), 5.24 (2H, s), 4.75˜4.65 (2H, m), 3.3˜3.2 (1H, m), 3.2˜3.1 (2H, m), 3.03 (3H, s), 2.47 (2H, q, J=7.6 Hz), 2.22˜2.16 (2H, m), 1.96˜1.84 (2H, m), 1.19 (3H, t, J=7.6 Hz).

Workup

concentrationAfter concentration in vacuo
customthe residue was purified by silica column chromatography with EtOAc/hexanes

Sources & evidence

ORD record: ord-5062ea31c8c949caba49fc14df4c8653
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975258B2

Reaction notes

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