3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one → 1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-pyrrolo[3,2-c]pyridin]-2'(1'H)-one

HRID 1715224Notes

Reaction equation

HRID 1715224 reaction equation
O[C:2]1[C:3]([C:11]2([CH2:26][OH:27])[C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:12]2=[O:25])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.OC1C(C2(CO)C3C(=NC=CC=3)N(CCCCC)C2=O)=CC2OCOC=2C=1>>[CH2:20]([N:13]1[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[C:11]2([C:3]3=[CH:4][C:5]4[O:9][CH2:8][O:7][C:6]=4[CH:10]=[C:2]3[O:27][CH2:26]2)[C:12]1=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 119628123-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneHCID 11962814HCID 11962814, compound

Product 1

HCID 119981911'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-pyrrolo[3,2-c]pyridin]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 1, and making non-critical variations using 3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one to replace 3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one, the title compound was obtained: 1H NMR (300 MHz, CDCl3) δ 8.51 (br, 1H), 8.28 (br, 1H), 6.97-6.87 (m, 1H), 6.51 (s, 1H), 6.08 (s, 1H), 5.90-5.84 (m, 2H), 6.87 (d, 1H), 4.67 (d, 1H), 3.86-3.60 (m, 2H), 1.78-1.63 (m, 2H), 1.44-1.27 (m, 4H), 0.89 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 177.0, 156.0, 150.7, 149.6, 149.4, 143.1, 142.6, 117.7, 113.9, 102.6, 101.7, 93.9, 80.0, 56.7, 40.7, 28.9, 27.1, 22.2, 13.9; MS (ES+) m/z 353.4 (M+1).

Sources & evidence

ORD record
ord-e5e47cc6bf9c4f84aee5cd52c8231762
Source dataset
uspto-grants-2010_09
Patent number
US07799798B2

Reaction notes

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