6-Methylpyridine-2-carboxylic acid → Methyl 3-[[(6-methyl-2-pyridinyl)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-carboxylate

HRID 218015

Reaction equation

HRID 218015 reaction equation
NC12CC3CC(CC(N[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=4)=[O:14])(C3)C1)C2.Cl.[CH3:23][O:24][C:25]([C:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][C:29]([NH2:37])([CH2:30]3)[CH2:28]1)[CH2:34]2)=[O:26].CC1N=C(C(O)=O)C=CC=1>>[CH3:23][O:24][C:25]([C:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][C:29]([NH:37][C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=4)=[O:14])([CH2:30]3)[CH2:28]1)[CH2:34]2)=[O:26]

Participants

4

Reactant 3

HCID 702826-Methylpyridine-2-carboxylic acidHCID 2852886Methyl 3-aminoadamantane-1-carboxylate hydrochlorideHCID 583586056-Methyl-pyridine-2-carboxylic acid (3-amino-adamantan-yl)-amide

Product 1

HCID 67083637Methyl 3-[[(6-methyl-2-pyridinyl)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-carboxylateYield 75%

Procedure

Intermediate 1 was also made via the same synthetic procedures for Intermediate 2 (see below). Starting from 3-amino-adamantane-1-carboxylic acid methyl ester hydrochloride (14.9 g, 60.8 mmol), coupling with 6-methyl-pyridine-2-carboxylic acid afforded 3-[(6-methyl-pyridine-2-carbonyl)-amino]-adamantane-1-carboxylic acid methyl ester (14.9 g, 75%). The methyl ester was then hydrolyzed to give 3-[(6-methyl-pyridine-2-carbonyl)-amino]-adamantane-1-carboxylic acid (12.2 g, 86%). Finally, the Curtius rearrangement of 3-[(6-methyl-pyridine-2-carbonyl)-amino]-adamantane-1-carboxylic acid (10.0 g, 31.8 mmol) yielded Intermediate 1 (8.48 g, 93%).

Sources & evidence

ORD record
ord-abff979b194947d49952cd09f9327ab8
Source dataset
uspto-grants-2012_06
Patent number
US08198275B2

Linked notes

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