HCID 86715162, compound → HCID 136408076, compound

HRID 2200841Notes

Reaction equation

HRID 2200841 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:14]=[C:15]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1.[CH:23]([NH:26][C:27](=[O:31])[O:28][CH2:29][I:30])([CH3:25])[CH3:24]>C(#N)C>[I-:30].[CH:23]([NH:26][C:27]([O:28][CH2:29][N+:19]1([CH3:22])[CH2:20][CH2:21][N:16]([C:15]2[C:4]3[CH:3]=[C:2]([CH3:1])[S:6][C:5]=3[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:14]=2)[CH2:17][CH2:18]1)=[O:31])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 86715162HCID 86715162, compoundHCID 135398745Olanzapine

Product 1

HCID 136408076HCID 136408076, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Olanzapine, (2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepine)[4134] (0.025 g, 0.086 mmol, 1.0 eq) in ACN was added iodomethyl isopropylcarbamate [6318] (0.20 g, 0.086 mmol, 1.0 eq) at RT. The reaction mixture was stirred at RT for four to 16 h. Reaction progress was monitored by TLC. Solvent was removed under vacuum to get a crude product. The crude product obtained was triturated with diethyl ether (5 ml×2) to give the desired product [294], 1-(((isopropylcarbamoyl)oxy)methyl)-1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazin-1-ium iodide (0.013 g, 41%) as yellow solid.

Workup

  1. customReaction progress
  2. customSolvent was removed under vacuum
  3. customto get a crude product
  4. customThe crude product obtained
  5. customwas triturated with diethyl ether (5 ml×2)

Sources & evidence

ORD record
ord-0c10b6a73dc9461ea858691ab29ac378
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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