5-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one → N2-(2-Oxo-2,3-dihydro-1H-indol-4-yl)-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)glycinamide

HRID 1669692Notes

Reaction equation

HRID 1669692 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:11][CH2:12][C:13]([OH:15])=O)[NH:3]1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:32](=[CH:33][CH:34]=1)[CH2:31][C:21]1([C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]1=[O:30])[CH2:20]2>>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:11][CH2:12][C:13]([NH:16][C:17]2[CH:18]=[C:19]3[C:32](=[CH:33][CH:34]=2)[CH2:31][C:21]2([C:29]4[C:24](=[N:25][CH:26]=[CH:27][CH:28]=4)[NH:23][C:22]2=[O:30])[CH2:20]3)=[O:15])[NH:3]1

Participants

3

Reactant 2

HCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×HCID 59322832N-(2-Oxo-2,3-dihydro-1H-indol-4-yl)glycine2×

Product 1

HCID 59648420N2-(2-Oxo-2,3-dihydro-1H-indol-4-yl)-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)glycinamide

Procedure

Essentially following the procedures described for Example 1, but using N-(2-oxo-2,3-dihydro-1H-indol-4-yl)glycine (described in Intermediate 8) in place of 3-phenylpropionic acid and (−)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (described in Intermediate 4) in place of (+)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, the title compound was obtained. MS: m/z=440 (M+1). HRMS: m/z=440.1750; calculated m/z=440.1717 for C25H22N5O3.

Sources & evidence

ORD record
ord-bb0a982709674ba48d7c6e362ee66972
Source dataset
uspto-grants-2011_08
Patent number
US07989624B2

Reaction notes

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