4-Hydroxypyrrolidine → HCID 59604095, compound

HRID 219583Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=3)[CH:27]=O)[N:20]=2)[N:10]=[N:9]1.[NH:32]1[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=3)[CH2:27][N:32]3[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]3)[N:20]=2)[N:10]=[N:9]1

Participants

Reactant 2

HCID 982104-Hydroxypyrrolidine

HCID 86648160HCID 86648160, compound

Product 1

HCID 59604095HCID 59604095, compound

Procedure

The title compound was prepared following the procedure described for Example 94, starting from 3-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde (100 mg; 0.24 mmol) and 3-pyrrolidinol (32.7 mg; 0.48 mmol) to give Example 134 as an off-white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.76-8.73 (2H, m), 7.97 (1H, s), 7.96-7.84 (2H, m), 7.76-7.69 (1H, m), 7.61 (2H, dd, J=4.5, 1.6 Hz), 7.59-7.49 (4H, m), 4.74 (1H, d, J=4.4 Hz), 4.29-4.21 (1H, m), 3.75-3.63 (2H, m), 2.75 (1H, dd, J=9.6, 6.2 Hz), 2.63 (1H, q, J=7.8 Hz), 2.51-2.45 (1H, m), 2.36 (1H, dd, J=9.6, 3.8 Hz), 2.10-1.99 (1H, m), 1.64-1.55 (1H, m). LC/MS (Method C): 484 (M+H)+. HPLC (Method E) Rt 2.13 min (Purity: 97.8%).

Sources & evidence

ORD record: ord-03dac193bf6943e7aa74e6337113d838
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202856B2

Reaction notes

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