HCID 11998204, compound → HCID 54582643, compound

HRID 645274Notes

Reaction equation

HRID 645274 reaction equation
[CH2:1]([N:6]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:8]2([CH2:20][CH2:19][C:18](=O)[C:17]3[C:9]2=[CH:10][C:11]2[O:15][CH2:14][O:13][C:12]=2[CH:16]=3)[C:7]1=[O:28])[CH2:2][CH2:3][CH2:4][CH3:5].C(N1C2C(=CC=CC=2)C2(C3C(=CC4OCOC=4C=3)C(=O)C2)C1=O)CCCC>>[CH2:1]([N:6]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:8]2([CH2:20][CH2:19][CH2:18][C:17]3[C:9]2=[CH:10][C:11]2[O:15][CH2:14][O:13][C:12]=2[CH:16]=3)[C:7]1=[O:28])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 11998204HCID 11998204, compoundHCID 545845861-pentyl-6''H-spiro[indoline-3,5''-naphtho[2,3-d][1,3]dioxole]-2,8''(7''H)-dione

Product 1

HCID 54582643HCID 54582643, compound

Procedure

Following the procedure as described in EXAMPLE 23, and making non-critical variations using 1-pentyl-6′H-spiro[indole-3,5′-naphtho[2,3-d][1,3]dioxole]-2,8′(1H,7′H)-dione to replace 1′-pentylspiro[indeno[5,6-d][1,3]dioxole-5,3′-indole]-2′,7(1′H,6H)-dione, the title compound was obtained (69%) as an oil: 1H NMR (300 MHz, CDCl3) δ 7.25 (td, 1H), 7.08-6.94 (m, 2H), 6.90 (d, 1H), 6.60 (s, 1H), 5.89 (s, 1H), 5.81-5.76 (m, 2H), 3.81-3.66 (m, 2H), 2.96-2.77 (m, 2H), 2.38-2.24 (m, 1H), 2.17-2.06 (m, 1H), 2.02-1.83 (m, 2H), 1.78-1.65 (m, 2H), 1.42-1.29 (m, 4H), 0.89 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 180.3, 146.7, 146.1, 142.4, 137.3, 131.6, 127.8, 127.8, 124.1, 122.5, 109.0, 108.3, 107.3, 100.7, 52.0, 40.0, 34.0, 29.4, 29.1, 27.1, 22.4, 18.8, 14.0; MS (ES+) m/z 364.1 (M+1).

Sources & evidence

ORD record
ord-972bee7352fe4ff2baff2bba81cee973
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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