Iodoacetamide → HCID 45280337, compound

HRID 422865Notes

Reaction equation

HRID 422865 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]3([C:27]4[C:18](=[CH:19][C:20]5[O:25][CH2:24][CH2:23][O:22][C:21]=5[CH:26]=4)[O:17][CH2:16]3)[C:8]2=[O:28])=[CH:4][CH:3]=1.OC1C=[C:34](C=CC=1)[CH2:35][N:36]1[C:44]2C(=CC=CC=2)C2(COC3C=C4C(=CC2=3)CCO4)[C:37]1=O.Cl.CN(C)CCCl.ICC(N)=O>>[CH3:37][N:36]([CH3:44])[CH2:35][CH2:34][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]3([C:27]4[C:18](=[CH:19][C:20]5[O:25][CH2:24][CH2:23][O:22][C:21]=5[CH:26]=4)[O:17][CH2:16]3)[C:8]2=[O:28])=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 3727IodoacetamideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 59352471HCID 59352471, compoundHCID 593525401'-(3-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 45280337HCID 45280337, compound

Procedure

Following the procedure as described in EXAMPLE 13 and making non-critical variations using 1′-(4-hydroxybenzyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1H)-one to replace 1′-(3-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, and 2-(dimethylamino)ethyl chloride hydrochloride to replace 2-iodoacetamide, 1′-{4-[2-(dimethylamino)ethoxy]benzyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1H)-one was obtained (26%) as a colorless solid: mp 77-79° C.; 1H NMR (300 MHz, CDCl3) δ 7.30-7.11 (m, 4H), 7.05-6.97 (m, 1H), 6.92-6.86 (m, 2H), 6.82-6.78 (m, 1H), 6.51 (s, 1H), 6.21 (s, 1H), 4.88 (ABq, J=77.2, 15.3 Hz, 2H), 4.79 (ABq, J=83.8, 8.9 Hz, 2H), 4.23-4.05 (m, 6H), 2.84-2.75 (m, 2H), 2.40 (s, 6H); 13C NMR (300 MHz, CDCl3) δ 177.5, 158.3, 155.2, 144.6, 142.1, 138.3, 132.3, 128.7, 127.9, 123.8, 123.3, 121.1, 114.9, 111.5, 109.3, 99.4, 80.2, 65.8, 64.5, 63.9, 58.2, 58.0, 45.8, 43.6; MS (ES+) m/z 472.8 (M+1).

Sources & evidence

ORD record
ord-60939db5fa224dcdbc91fe95b5db3118
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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