1,2-Diaminocyclohexane → HCID 178463823, compound

HRID 452122Notes

Reaction equation

HRID 452122 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16](C)(C)C)CO)=[CH:6][CH:5]=1)[CH3:2].S(Cl)(Cl)=O.Br[C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[C:30]([NH2:35])[CH:29]=1.[F-].[Cs+].N[CH:39]1CCCCC1N>[Cu](I)I.C(O)=O>[NH:35]1[C:30]2[CH:29]=[CH:28][C:33]([N:13]3[C@@H:10]([C:7]4[CH:6]=[CH:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:21][CH3:22])=[CH:9][CH:8]=4)[CH2:16][O:15][C:14]3=[O:20])=[CH:32][C:31]=2[N:34]=[CH:39]1

Participants

8

Reactant 5

HCID 46101,2-DiaminocyclohexaneHCID 24386Thionyl ChlorideHCID 25953Cesium fluorideHCID 3235934-Bromobenzene-1,2-diamineHCID 57488496HCID 57488496, compound

Product 1

HCID 178463823HCID 178463823, 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-(diethylamino)phenyl)-2-hydroxyethylcarbamate (0.500 g, 21.623 mmol), thionyl chloride (0.95 mL, 12.98 mmol, 4-bromo1,2-diamino benzene (219 mg, 1.175 mmol), cesium fluoride (324 mg, 2.136 mmoles) and copper iodide (30 mg, 0.160 mmoles), 1,2-diaminocyclohexane (0.02, 0.1602 mmoles), formic acid (5 mL). Yield: 0.05 g (0.6%). MS m/z 351.4 (M+H)+; 1H-NMR (400 MHz, DMSO-d6): δ 12.44 (d, 1H); 8.17 (d, 1H); 7.56-7.13 (m, 5H); 6.55 (d, 2H); 5.54 (t, 1H); 4.75 (t, 1H); 4.09 (t, 1H); 3.39-3.20 (m, 4H); 1.23-0.98 (m, 6H), HPLC (λ=214 nm, [A]: rt 6.04 min (97.7%).

Workup

  1. customThe compound was synthesized
  2. customrt 6.04 min (97.7%)

Sources & evidence

ORD record
ord-6e1d6895da9b46639e8a8ed8c1da6ee8
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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