3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one → 4'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,6'-thieno[3,2-b]pyrrol]-5'(4'H)-one
Reaction equation
O[C:2]1[C:3]([C:11]2([CH2:25][OH:26])[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:13]3[CH:22]=[CH:23][S:24][C:12]2=3)=[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>>[CH2:17]([N:14]1[C:15](=[O:16])[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:26][CH2:25]2)[C:12]2[S:24][CH:23]=[CH:22][C:13]1=2)[CH2:18][CH2:19][CH2:20][CH3:21]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in EXAMPLE 1, and making non-critical variations using 6-(6-hydroxy-1,3-benzodioxol-5-yl)-6-(hydroxymethyl)-4-pentyl-4,6-dihydro-5H-thieno[3,2-b]pyrrol-5-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 (13%): 1H NMR (300 MHz, DMSO-d6) δ 7.30 (d, 1H), 6.79 (d, 1H), 6.46 (s, 1H), 6.16 (s, 1H), 5.88-5.83 (m, 2H), 4.86 (d, 1H), 4.62 (d, 1H), 3.80-3.56 (m, 2H), 1.73-1.11 (m, 6H), 0.88 (t, 3H); MS (ES+) m/z 358.3 (M+1).
Sources & evidence
- ORD record
- ord-d36f8d0485c049c3ae4c984e82b093fe
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799798B2
Reaction notes
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