Ethyl Acetate → HCID 178461311, compound

HRID 1810067Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.ClC1C=CC=CC=1COCCN([C@H]1CC[C@H](C)CC1)[C:24](=[O:39])[NH:25][C:26]1[S:27][C:28]([S:31]CC(C)(C)C(O)=O)=[CH:29][N:30]=1.C([O:53][C:54](=[O:56])[CH3:55])C>>[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:24](=[O:39])[NH:25][C:26]2[S:27][C:28]([S:31][CH2:55][C:54]([OH:53])=[O:56])=[CH:29][N:30]=2)[CH2:4][CH2:3]1

Participants

Reactant 3

HCID 8857Ethyl Acetate

HCID 43178505HCID 43178505, compound

HCID 178454946HCID 178454946, compound

Product 1

HCID 178461311HCID 178461311, compound

Procedure

A mixture of 4-formylpyridine (0.88 g, 8.25 mmol), trans-4-methyl-cyclohexylamine hydrochloride (0.93 g, 8.25 mmol) and NaBH3CN (1.3 g, 20.6 mmol) in MeOH (50 mL) and AcOH (1.5 mL) was refluxed for 1.5 h. The heating was discontinued and the reaction mixture was left at rt for 2 days. The volatiles were removed in vacuo and the residue was divided between aqueous NaHCO3 and DCM. The DCM phase was concentrated in vacuo. Purification on preparative HPLC gave the TFA salt of (4-methyl-cyclohexyl)-pyridin-4-ylmethyl-amine. The amine was coupled and hydrolyses using the procedure described in the procedure for the preparation of 3-{2-[3-[2-(2-chloro-benzyloxy)-ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-2,2-dimethyl-propionic acid using 2-aminothiazol-5-ylsulfanyl)acetic acid ethyl ester

Sources & evidence

ORD record: ord-dca7bfe219214062bf70ece2d6fdf7d7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362049B2

Reaction notes

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