p-Toluenesulfonic acid → HCID 59447968, compound

HRID 1916297Notes

Reaction equation

HRID 1916297 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[C:27]3[C:26]4[C:21](=[CH:22][C:23]([C:28](=[O:30])[NH2:29])=[CH:24][CH:25]=4)[NH:20][C:19]=3[N:18]=[CH:17][N:16]=2)[CH2:10]1)(C)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:7][CH2:8][CH:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[C:27]3[C:26]4[C:21](=[CH:22][C:23]([C:28]([NH2:29])=[O:30])=[CH:24][CH:25]=4)[NH:20][C:19]=3[N:18]=[CH:17][N:16]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59447976HCID 59447976, compound

Product 1

HCID 59447968HCID 59447968, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

[4-(7-Carbamoyl-9H-pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester (5.5 mg, 0.013 mmol) was suspended in methanol and loaded onto a MP-TsOH SPE cartridge which had been pre-conditioned with methanol. The deprotected product was then eluted off using 2 N ammonia in methanol and concentrated in vacuo to give the title compound as an off-white solid (4 mg, 0.012 mmol). LC-MS (2) Rt 1.08 min; m/z 327 (ES+).

Workup

  1. washThe deprotected product was then eluted off
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01f8440e056a4530b247c9473af3e2ca
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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