HCID 59352445, compound → HCID 45280395, compound

HRID 422864Notes

Reaction equation

[OH:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]3([CH2:19][O:18][C:17]4[CH:20]=[C:21]5[C:25](=[CH:26][C:16]3=4)[CH2:24][CH2:23][O:22]5)[C:8]2=[O:27])=[CH:4][CH:3]=1.OC1C=C(C=CC=1)C[N:35]1C2C(=CC=CC=2)[C:37]2(COC3C=C4C(=CC2=3)CCO4)[C:36]1=[O:55]>>[O:27]=[C:8]1[C:9]2([CH2:19][O:18][C:17]3[CH:20]=[C:21]4[C:25](=[CH:26][C:16]2=3)[CH2:24][CH2:23][O:22]4)[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:37][C:36]([NH2:35])=[O:55])=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 59352445HCID 59352445, compound

HCID 593525401'-(3-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 45280395HCID 45280395, compound

Procedure

Following the procedure as described in EXAMPLE 13 and making non-critical variations using 1′-(4-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one to replace 1′-(3-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, 2-{4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetamide was obtained (81%) as a colorless solid: mp 215-216° C.; 1H NMR (300 MHz, CDCl3) δ 7.35-7.29 (m, 2H), 7.25-7.14 (m, 2H), 7.06-6.99 (m, 1H), 6.93-6.87 (m, 2H), 6.83-6.78 (m, 1H), 6.52 (br s, 1H), 6.46 (s, 1H), 6.43 (s, 1H), 5.67 (br s, 1H), 5.04-4.95 (m, 2H), 4.85-4.76 (m, 1H), 4.73-4.66 (m, 1H), 4.59-4.50 (m, 2H), 4.48 (s, 2H), 3.10-2.90 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 177.9, 170.7, 161.8, 160.3, 156.7, 142.0, 132.7, 129.6, 129.0, 128.6, 123.9, 123.4, 120.1, 119.9, 118.8, 115.0, 109.1, 93.2, 80.6, 72.4, 67.1, 57.7, 43.4, 29.0; MS (ES+) m/z 443.0 (M+1).

Sources & evidence

ORD record: ord-440eb2fd046740beb40a6a0d303cf791
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101647B2

Reaction notes

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