L-Alaninol → HCID 86601359, compound

HRID 1295673Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22](F)[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[NH2:27][C@@H:28]([CH3:31])[CH2:29][OH:30]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:27][CH:28]([CH3:31])[CH2:29][OH:30])[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

The 2′-fluoro-3,4,5, 6-tetrahydro-2H-[1,4′]bipyridinyl-4-carboxylic acid [1 -(3-chloro-phenyl)-2-hydroxy-ethyl]-amide compound (10 mg, 0.026 mmol) was combined with (S)-2-amino-propanol (0.2 mL) in DMSO and heated in an oil bath to 160° C. for 18 hours. The crude mixture was pipetted onto a preparative TLC plate (1 mm silica) and the compound eluted with ethyl acetate. Isolation of the most UV active band afforded 2.6 mg of the title product as a colorless oil. Rt=4.40 minutes, LCMS 447.3 (M=1), 1H NMR δ 7.66 (s, 1H) 7.32–7.20 (m, 4H) 6.34 (NH) 5.94 (s, 1H) 5.07–5.06 (m, 1H) 4.17 (m, 1H) 3.90 (m, 1H) 3.62 (m, 2H) 3.36 (m, 2H) 2.85 (m, 1H) 2.63 (m, 2H) 2.33 (m, 1H) 2.08 (s, 3H) 1.94 (m, 4H) 1.19 (d, 3H).

Workup

washthe compound eluted with ethyl acetate

Sources & evidence

ORD record: ord-d9235265309c45c89bc27c99d9b6d2a5
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244735B2

Reaction notes

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