5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid → [(Z)-[amino-[(2S)-1-(cyclohexylmethylsulfonyl)piperidin-2-yl]methylidene]amino] 5-[(1,3-dioxoisoindol-2-yl)methyl]furan-2-carboxylate

HRID 397701Notes

Reaction equation

HRID 397701 reaction equation
[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2/[C:17](=[N:19]/[OH:20])/[NH2:18])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[N:23]1[CH2:32][C:33]1[O:37][C:36]([C:38](O)=[O:39])=[CH:35][CH:34]=1>>[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2/[C:17](=[N:19]/[O:20][C:38]([C:36]2[O:37][C:33]([CH2:32][N:23]3[C:24](=[O:31])[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22]3=[O:21])=[CH:34][CH:35]=2)=[O:39])/[NH2:18])(=[O:9])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 230007015-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acidHCID 59085897HCID 59085897, compound

Product 1

HCID 59085909[(Z)-[amino-[(2S)-1-(cyclohexylmethylsulfonyl)piperidin-2-yl]methylidene]amino] 5-[(1,3-dioxoisoindol-2-yl)methyl]furan-2-carboxylate

Procedure

The title compound was prepared by a similar method to Preparation 5 from (Z)-(2S)-1-[(cyclohexylmethyl)sulfonyl]-N′2-hydroxy-2-piperidinecarboximidamide [see Preparation 28] and 5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid (see Preparation 98], to afford (Z)-(2S)-1-[(cyclohexylmethyl)sulfonyl]-N′2-[(5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furylcarbonyl)oxy]-2-piperidinecarboximidamide as a yellow oil.

Workup

  1. customPreparation 98],

Sources & evidence

ORD record
ord-3f143839cf044ab98abd08d740ed41a3
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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