1,2-Diaminocyclohexane → HCID 178495929, compound

HRID 452123Notes

Reaction equation

HRID 452123 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:23][CH2:24][O:25][CH3:26])[C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([NH:15][C:16](=[O:22])[O:17][C:18](C)(C)C)CO)=[CH:8][CH:7]=1.S(Cl)(Cl)=O.Br[C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([NH2:39])[CH:33]=1.[F-].[Cs+].N[CH:43]1CCCCC1N>[Cu](I)I.C(O)=O>[NH:39]1[C:34]2[CH:33]=[CH:32][C:37]([N:15]3[C@@H:12]([C:9]4[CH:8]=[CH:7][C:6]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:23][CH2:24][O:25][CH3:26])=[CH:11][CH:10]=4)[CH2:18][O:17][C:16]3=[O:22])=[CH:36][C:35]=2[N:38]=[CH:43]1

Participants

8

Reactant 5

HCID 46101,2-DiaminocyclohexaneHCID 24386Thionyl ChlorideHCID 25953Cesium fluorideHCID 3235934-Bromobenzene-1,2-diamineHCID 57488497HCID 57488497, compound

Product 1

HCID 178495929HCID 178495929, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 284Formic AcidSolvent

Procedure

The compound was synthesized according to method 6 starting from tert-butyl (R)-1-(4-(bis(2-methoxyethyl)amino)phenyl)-2-hydroxyethylcarbamate (0.350 g, 0.951 mmol), thionyl chloride (0.55 mL, 7.608 mmol), 4-bromo-1,2-diamino benzene (111 mg, 0.598 mmol), cesium fluoride (165 mg, 1.08 mmoles) and copper iodide (15 mg, 0.081 mmoles), 1,2-diaminocyclohexane (0.06, 0.598 mmoles) formic acid (5 mL). Yield: 0.04 g (10.8%). MS m/z 411.4 (M+H)+; 1H-NMR 400 MHz, CDCl3): δ 7.89 (d, 1H); 7.60-7.45 (m, 2H); 7.26-7.11 (merged with CDCl3, 3H); 6.61 (d, 2H); 5.60 (t, 1H); 4.77 (t, 1H); 4.33 (t, 1H); 3.60-3.49 (m, 8H); 3.32 (s, 6H), HPLC (λ=214 nm, [A]: rt 10.09 min (96%).

Workup

  1. customThe compound was synthesized
  2. customrt 10.09 min (96%)

Sources & evidence

ORD record
ord-236e4ddceb9d4f5c825ab5cdfad725a5
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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