p-Toluenesulfonic acid → HCID 59447963, compound

HRID 1916305Notes

Reaction equation

HRID 1916305 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH:20]([CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:19]4)=[N:16][CH:15]=[N:14][C:10]=3[NH:11]2)=[CH:7][CH:6]=1)=[O:4].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:25][CH2:24][CH:20]1[CH2:19][N:18]([C:17]2[C:9]3[C:8]4[C:12](=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=4)[NH:11][C:10]=3[N:14]=[CH:15][N:16]=2)[CH2:23][CH2:22][O:21]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68517179HCID 68517179, compound

Product 1

HCID 59447963HCID 59447963, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 mg (0.045 mmol) of 4-[2-(tert-butoxycarbonylamino-methyl)-morpholin-4-yl]-9H-pyrimido[4,5-b]indole-7-carboxylic acid methyl ester (from Synthesis 3-1-F) was dissolved in methanol and deprotected on a MP-TsOH cartridge. The product was eluted with 2 N ammonia in methanol and concentrated in vacuo to give 11.6 mg (0.034 mmol, 75%) of the title compound as a beige solid. LC-MS (1) Rt 1.68 min; m/z (ES+) 342. 1H NMR (ppm, MeOD) δ 8.41 (1H, d, J=0.8 Hz), 8.08 (1H, s), 7.88 (1H, dd, J=8.5, 1.5 Hz), 7.80 (1H, d, J=8.3 Hz), 4.21 (1H, d, J=12.6 Hz), 4.13 (1H, d, J=13.1 Hz), 4.06 (1H, dd, J=11.6, 2.5 Hz), 3.93 (3H, s), 3.81 (1H, td, J=11.9, 2.0 Hz), 3.71-3.69 (1H, m), 3.34 (2H, d, J=0.8 Hz), 3.00 (1H, dd, J=12.6, 10.8 Hz), 2.77 (1H, s), 2.76 (1H, d, J=2.5 Hz).

Workup

  1. washThe product was eluted with 2 N ammonia in methanol
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8541227e6f5b4a34a0b3b49aaab0f45d
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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