HCID 136377197, compound → HCID 136252346, compound

HRID 624543Notes

Reaction equation

HRID 624543 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH:21]=[C:20]([CH3:22])[S:19][C:10]=3[NH:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:4][CH:3]1[CH2:23][N:24]1C(=O)C2C(=CC=CC=2)C1=O>CN>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH:21]=[C:20]([CH3:22])[S:19][C:10]=3[NH:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:4][CH:3]1[CH2:23][NH2:24]

Participants

3

Reactant 1

HCID 136377197HCID 136377197, compound

Product 1

HCID 136252346HCID 136252346, compound

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

A solution 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, prepared as described in the previous step, (1.0 g) in ethanolic methylamine (20 mL) was stirred at ambient temperature overnight. The solvent was removed under vacuum and the residue purified by HPLC to give the hydrochloride salt of (1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazin-2-yl)methanamine as a red solid. 1H NMR (400 MHz, MeOD) δ 7.46-7.44 (m, 1H), 7.31-7.48 (m, 1H), 7.19-7.15 (m, 1H), 6.97-6.95 (m, 1H), 6.74 (s, 1H), 4.80-4.71 (br, 1H), 4.28-4.20 (br, 2H), 4.07-4.04 (br, 2H), 3.82-3.70 (br, 3H), 3.53-3.48 (m, 1H), 3.18 (s, 3H), 2.42 (m, 3H); ESI-MS (M+1): 342 calc. for C18H23N5S Exact Mass: 341.17.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-c8bff0b135704d88a4ef08256ffda253
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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