Dimethylamine → HCID 59352114, compound

HRID 1407938Notes

Reaction equation

HRID 1407938 reaction equation
[CH3:1][NH:2][CH3:3].N1CCOCC1.Cl[C:11]1[N:16]=[C:15]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3([C:38]4[C:29](=[CH:30][C:31]5[O:36][CH2:35][CH2:34][O:33][C:32]=5[CH:37]=4)[O:28][CH2:27]3)[C:19]2=[O:39])[CH:14]=[CH:13][CH:12]=1.ClC1N=CC(CN2C3C(=CC=CC=3)C3(C4C(=CC5OCCOC=5C=4)OC3)C2=O)=CC=1>>[CH3:1][N:2]([CH3:3])[C:11]1[N:16]=[C:15]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3([C:38]4[C:29](=[CH:30][C:31]5[O:36][CH2:35][CH2:34][O:33][C:32]=5[CH:37]=4)[O:28][CH2:27]3)[C:19]2=[O:39])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 8083MorpholineHCID 59352412HCID 59352412, compoundHCID 86697478HCID 86697478, compound

Product 1

HCID 59352114HCID 59352114, compound

Procedure

Following the procedure as described in EXAMPLE 32 and making non-critical variations using dimethylamine (40% w/w in water) to replace morpholine and 1′-[(6-chloropyridin-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 1′-[(6-chloropyridin-3-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, 1′-{[6-(dimethylamino)pyridin-2-yl]methyl}-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (44%) as a colorless solid: mp 196-197° C.; 1H NMR (300 MHz, CDCl3) δ7.45-7.34 (m, 1H), 7.24-7.11 (m, 2H), 7.06-6.94 (m, 2H), 6.52-6.46 (m, 2H), 6.42-6.35 (m, 1H), 6.28 (s, 1H), 4.91 (ABq, J=53.2, 15.3 Hz, 2H), 4.80 (ABq, J=84.8, 9.1 Hz, 2H), 4.23-4.07 (m, 4H), 3.04 (s, 6H); 13C NMR (300 MHz, CDCl3) δ 177.4, 159.0, 155.3, 153.3, 144.5, 142.7, 138.2, 137.9, 132.2, 128.6, 123.5, 123.1, 121.2, 111.7, 109.9, 108.8, 104.5, 99.3, 80.3, 64.5, 63.9, 58.1, 46.0, 37.8; MS (ES+) m/z 430.0 (M+1).

Sources & evidence

ORD record
ord-44171845d1f14345838636b8f2a82c27
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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