Benzylamine → Tirbanibulin

HRID 403217Notes

Reaction equation

HRID 403217 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23](OC)=[O:24])=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(OC)C=CC=CC=1>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]([NH:34][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:24])=[N:20][CH:21]=3)=[CH:14][CH:15]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 44185422Methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate

Product 1

HCID 23635314Tirbanibulin

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

The resulting methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate (7) and benzyl amine were coupled in anisole at high temperature to afford 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide (Compound 134). An HCl solution formed by adding acetyl chloride to absolute ethanol was added to Compound 134 to form the bis-HCl salt, 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride, (KX2-di-HCl).

Sources & evidence

ORD record
ord-9475adc6d52b4122a32458f9d31010c3
Source dataset
uspto-grants-2014_06
Patent number
US08748423B2

Reaction notes

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