1,2-Dichloroethane → 2-(2-Oxo-3-pyridin-2-ylimidazolidin-1-yl)-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acetamide

HRID 1442880Notes

Reaction equation

HRID 1442880 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][N:3]1[CH2:13][C:14]([OH:16])=O.[NH2:17][C:18]1[CH:19]=[C:20]2[C:33](=[CH:34][CH:35]=1)[CH2:32][C:22]1([C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]1=[O:31])[CH2:21]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][N:3]1[CH2:13][C:14]([NH:17][C:18]1[CH:19]=[C:20]2[C:33](=[CH:34][CH:35]=1)[CH2:32][C:22]1([C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]1=[O:31])[CH2:21]2)=[O:16]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 184426422-oxo-3-(2-pyridinyl)-1-Imidazolidineacetic acid2×HCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Product 1

HCID 116266352-(2-Oxo-3-pyridin-2-ylimidazolidin-1-yl)-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-oxo-3-pyridin-2-ylimidazolidin-1-yl)acetic acid (22 mg, 0.10 mmol, described in Intermediate 14), (−)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (25 mg, 0.10 mmol, described in Intermediate 4), EDC (19 mg, 0.10 mmol), HOBT (15 mg, 0.10 mmol), and N,N-diisopropylethylamine (0.0138 mL, 0.10 mmol) is stirred in DMF (0.5 mL) at ambient temperature for 18 h. The crude mixture is purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H-90:10:0.1 to 5:95:0.1. Lyophilization provides the title compound.

Workup

  1. customThe crude mixture is purified directly by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-74ccc18e77a14d2c9434817a6ae145a9
Source dataset
uspto-grants-2010_02
Patent number
US07659300B2

Reaction notes

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