1,4-Dioxane hydrochloride → C-[4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-yl]-methylamine

HRID 1916283Notes

Reaction equation

HRID 1916283 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][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]=3[N:18]=[CH:17][N:16]=2)[CH2:10]1)(C)(C)C.Cl.O1CCOCC1>CO>[N:18]1[C:19]2[NH:20][C:21]3[C:26]([C:27]=2[C:15]([N:11]2[CH2:12][CH2:13][O:14][CH:9]([CH2:8][NH2:7])[CH2:10]2)=[N:16][CH:17]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59447938[4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 57391918C-[4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-yl]-methylamineYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [4-(9H-pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester (0.021 g, 0.548 mmol) and 4M HCl-dioxane (1 mL) in methanol (5 mL) was stirred at room temperature for 2.5 hours. The solution was evaporated to dryness and purified by Ion exchange on SCX-II acidic resin (2 g) eluting with methanol, then 2 M ammonia-methanol. The basic fractions were combined. Preparative silica TLC, eluting with 1% ammonia—9% methanol—90% dichloromethane, gave the title compound (0.007 g, 0.025 mmol, 46%) as a beige powder. 1H NMR (500 MHz, CD3OD) δ 2.75-2.80 (2H, m), 3.00-3.06 (1H, m), 3.35-3.40 (1H, m), 3.75-3.85 (1H, m), 3.90 (1H, dd, J=10.10 Hz), 4.10-4.13 (1H, m), 4.19 (1H, d, J=13 Hz), 4.25 (1H, d, J=13 Hz), 7.35 (1H, dd, J=8.8 Hz), 7.47 (1H, dd, J=8.8 Hz), 7.57 (1H, d, J=8 Hz), 7.79 (1H, d, J=8 Hz), 8.46 (1H, s); LC-MS (3) Rt 1.98 min; m/z (ESI) 284 [MH+].

Workup

  1. customThe solution was evaporated to dryness
  2. custompurified by Ion exchange on SCX-II acidic resin (2 g)
  3. washeluting with methanol
  4. washPreparative silica TLC, eluting with 1% ammonia—9% methanol—90% dichloromethane

Sources & evidence

ORD record
ord-e20f5f89200d48bbac87a9f5eabf74f8
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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