Trimethylaluminum → HCID 59854177, compound

HRID 2374700Notes

Reaction equation

HRID 2374700 reaction equation
[NH2:1][C:2]1[C:3]([O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=O.Br[C:27]1[C:32]([CH:33]=O)=[C:31]([CH3:35])[CH:30]=[CH:29][N:28]=1.C[Al](C)C.[CH3:40][NH:41][CH2:42][CH:43]1[CH2:46][CH2:45][CH2:44]1>>[CH:43]1([CH2:42][N:41]([CH3:40])[C:5]([C:4]2[CH:9]=[CH:10][C:11]3[C:2]([C:3]=2[O:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:1][C:27]2[N:28]=[CH:29][CH:30]=[C:31]([CH3:35])[C:32]=2[CH:33]=3)=[O:7])[CH2:46][CH2:45][CH2:44]1

Participants

5

Reactant 4

HCID 16682925TrimethylaluminumHCID 198302711-Cyclobutyl-N-methylmethanamineHCID 59854193HCID 59854193, compoundHCID 59854220HCID 59854220, compound

Product 1

HCID 59854177HCID 59854177, compound

Procedure

For example, methyl 3-amino-2-diphenylmethoxybenzoate A28.8 is reacted, as described above, with 2-bromo-4-methylpyridine-3-carboxaldehyde A28.9 (Arkivoc, 2000, 1, 52) to produce after cyclization, the tricyclic ester A28.10. The ester is then reacted with trimethylaluminum and N-methylcyclobutylmethylamine A28.11 to give 9-benzhydryloxy-4-methyl-benzo[b][1,8]naphthyridine-8-carboxylic acid cyclobutylmethyl-methyl-amide A28.12. Benzylic bromination then gives the bromomethyl analog A28.13. The latter compound is heated at 120° C. with excess of a trialkyl phosphite to produce after deprotection the phosphonate A28.14.

Workup

  1. customis reacted
  2. customto produce after cyclization

Sources & evidence

ORD record
ord-d62bfead7d074a5b86157287ad89cc7b
Source dataset
uspto-grants-2008_12
Patent number
US07462721B2

Reaction notes

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