HCID 10538481, compound → HCID 69992501, compound

HRID 611471Notes

Reaction equation

O=C1N(C[C:9]([OH:11])=[O:10])C(C2C=CC(F)=CC=2)=NC=C1.[ClH:19].[CH3:20][C:21]([C:29]1[O:30][C:31]([CH:34]([OH:40])[C@@H:35]([NH2:39])[CH:36]([CH3:38])[CH3:37])=[N:32][N:33]=1)([CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[ClH:19].[CH3:20][C:21]([C:29]1[O:30][C:31]([CH:34]([OH:40])[C@@H:35]([NH2:39])[CH:36]([CH3:37])[CH3:38])=[N:32][N:33]=1)([CH3:28])[C:22]1[CH:23]=[CH:24][C:25]2[O:10][CH2:9][O:11][C:26]=2[CH:27]=1

Participants

Reactant 2

HCID 10538481HCID 10538481, compound

HCID 69994072HCID 69994072, compound

Product 1

HCID 69992501HCID 69992501, compound

Procedure

The intermediate 2-[6-oxo-2-(4-fluorophenyl)-1,6-dihydro-1-pyrimidinyl]-N-[1-(2-[5-(α,α-dimethylbenzyl)-1,3,4-oxadiazolyl]hydroxymethyl)-2-(S)-methylpropyl]acetamide was prepared in an analoguous manner as described in Example 1 E using [6-oxo-2-(4-fluorophenyl)-1,6-dihydro-1-pyrimidinyl]acetic acid. and 1-[2-(α,α-dimethylbenzyl)-1,3,4-oxadiazolyl]-2-(S)-amino-3-methylbutan-1-ol hydrochloride. The intermediate 1-[2-(α,α-dimethyl-3,4-methylenedioxybenzyl)-1,3,4-oxadiazolyl]-2-(S)-amino-3-methylbutan-1-ol hydrochloride was prepared using a similar procedure as described in Example 1 D. The heterocyclic intermediate 2-(α,α-dimethylbenzyl)-1,3,4-oxadiazole gave the following physical data.

Workup

customThe intermediate 2-[6-oxo-2-(4-fluorophenyl)-1,6-dihydro-1-pyrimidinyl]-N-[1-(2-[5-(α,α-dimethylbenzyl)-1,3,4-oxadiazolyl]hydroxymethyl)-2-(S)-methylpropyl]acetamide was prepared in an analoguous manner

Sources & evidence

ORD record: ord-300e923b05b04e70b36c7d0e57044806
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06001814

Reaction notes

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