Diisopropylethylamine → HCID 136377197, compound

HRID 624542Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19].[CH3:20][C:21]1[S:35][C:24]2[NH:25][C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[N:28]=[C:29](N)[C:23]=2[CH:22]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:29]2[C:23]3[CH:22]=[C:21]([CH3:20])[S:35][C:24]=3[NH:25][C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[N:28]=2)[CH2:4][CH:3]1[CH2:8][N:9]1[C:10](=[O:19])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]1=[O:18]

Participants

Conditions

Temperature: 170 °C

Procedure

A solution of 2-((1-methylpiperazin-2-yl)methyl)isoindoline-1,3-dione, prepared as described in step D, (100 mg, 0.38 mmol), 2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-amine, prepared as described in step G, (150 mg, 0.52 mmol) and diisopropylethylamine (0.49 g, 3.8 mmol) in dimethylsulfoxide (0.5 mL) was stirred at 170° C. for 2 hrs. The reaction was diluted with water and extracted with ethyl acetate. The organic phase was concentrated and the residue purified by column to give 15 mg of 2-((1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazin-2-yl)methyl)isoindoline-1,3-dione. 1H NMR (400 MHz, CDCl3) δ 7.76-7.73 (m, 1H), 7.45-7.35 (m, 3H), 7.18-7.17 (m, 1H), 6.98-6.95 (m, 2H), 6.75-6.73 (m, 1H), 6.46 (s, 1H), 4.28-4.25 (m, 1H), 3.96-6.92 (m, 1H), 3.71-3.64 (m, 3H), 3.47-3.41 (m, 1H), 3.29-3.28 (m, 1H), 3.12-3.09 (m, 1H), 2.87-2.86 (m, 1H), 2.67-2.53 (m, 3H), 2.28 (s, 3H).

Workup

customprepared
extractionextracted with ethyl acetate
concentrationThe organic phase was concentrated
customthe residue purified by column

Sources & evidence

ORD record: ord-e422481c0b1a486ca7ab61f3441d9269
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303041B2

Reaction notes

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