2-(Methylsulfonyl)ethanamine → (4-Phenoxyphenyl)-(7-(5-(2-(methanesulphonyl)ethylaminomethyl)furan-2-yl)-quinolin-4-yl)amine

HRID 2215739Notes

Reaction equation

HRID 2215739 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[O:29][C:28]([CH:30]=O)=[CH:27][CH:26]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][S:33]([CH2:36][CH2:37][NH2:38])(=[O:35])=[O:34]>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[O:29][C:28]([CH2:30][NH:38][CH2:37][CH2:36][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:27][CH:26]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 43405612-(Methylsulfonyl)ethanamineHCID 219519195-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)furan-2-carbaldehyde

Product 1

HCID 21952211(4-Phenoxyphenyl)-(7-(5-(2-(methanesulphonyl)ethylaminomethyl)furan-2-yl)-quinolin-4-yl)amine

Procedure

5-(4-(4-phenoxyphenylamino)-quinolin-7-yl)furan-2-carbaldehyde (0.05 g) was reacted with 2-(methanesulphonyl)ethylamine (0.075 g) according to procedure D. Acidification with acetic acid (0.5 ml) followed by purification using a ion-exchange (SCX) Bond Elut™ cartridge, eluting with methanol-ammonia (9:1), concentration and trituration with diethylether afforded an off-white solid; δH [2H6] DMSO 8.44 (1H, d), 8.41 (1H, d), 8.11 (1H, s), 7.85 (1H, d), 7.44–7.35 (4H, m), 7.18–7.03 (6H, m), 6.79 (1H, d), 6.47 (1H, d), 3.82 (2H, s), 3.01 (2H, t); m/z 514 (M+1)+.

Workup

  1. customAcidification with acetic acid (0.5 ml) followed by purification
  2. washeluting with methanol-ammonia (9:1), concentration and trituration with diethylether
  3. customafforded an off-white solid

Sources & evidence

ORD record
ord-3934240d1b1f4a748f3453a35c4e1f87
Source dataset
uspto-grants-2006_09
Patent number
US07109333B2

Reaction notes

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