Dimethylamine, hydrochloride → 1'-{[5-(dimethylamino)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

HRID 2385561Notes

Reaction equation

HRID 2385561 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N1CC[C@@H](N)C1)(OC(C)(C)C)=O.Br[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]3([C:46]4[C:37](=[CH:38][C:39]5[O:44][CH2:43][CH2:42][O:41][C:40]=5[CH:45]=4)[O:36][CH2:35]3)[C:27]2=[O:47])=[N:23][CH:24]=1.BrC1C=CC(CN2C3C(=CC=CC=3)C3(C4C=C(F)C(F)=CC=4OC3)C2=O)=CC=1>>[CH3:2][N:3]([CH3:4])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]3([C:46]4[C:37](=[CH:38][C:39]5[O:44][CH2:43][CH2:42][O:41][C:40]=5[CH:45]=4)[O:36][CH2:35]3)[C:27]2=[O:47])=[N:23][CH:24]=1

Participants

5

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 593524831'-(4-bromobenzyl)-5,6-difluorospiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 59352743HCID 59352743, compound

Product 1

HCID 593526071'-{[5-(dimethylamino)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 33.1 and making non-critical variations using dimethylamine hydrochloride to replace (R)-(+)-1-Boc-3-aminopyrrolidine, and 1′-[(5-bromopyridin-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 1′-(4-bromobenzyl)-5,6-difluorospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 1′-{[5-(dimethylamino)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (23%) as a beige solid: mp 229-236° C.; 1H NMR (300 MHz, CDCl3) δ8.06 (d, J=2.7 Hz, 1H), 7.22-6.92 (m, 6H), 6.50 (s, 1H), 6.27 (s, 1H), 5.11 (d, J=15.3 Hz, 1H), 4.94 (d, J=9.0 Hz, 1H), 4.87 (d, J=15.3 Hz, 1H), 4.65 (d, J=8.7 Hz, 1H), 4.21-4.11 (m, 4H), 2.96 (s, 6H); 13C NMR (75 MHz, CDCl3) δ177.4, 155.3, 145.5, 144.5, 142.8, 142.4, 138.3, 134.1, 132.3, 128.8, 123.6, 123.2, 122.0, 121.2, 119.8, 111.7, 109.9, 99.3, 80.2, 64.5, 63.9, 58.1, 45.7, 40.1; MS (ES+) m/z 430.1 (M+1).

Sources & evidence

ORD record
ord-8914df54595d42f591f52c013903053a
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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