1,2-Diaminocyclohexane → HCID 178519151, compound

HRID 706331Notes

Reaction equation

HRID 706331 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CBr.C1([PH+]([C:27]2[CH:32]=[CH:31]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClO[C:35]([CH3:38])(C)[CH3:36].[C:39](=[O:49])([O:41]C(OC(C)(C)C)=O)[NH2:40].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H]([C:96]4[CH:105]=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.S(Cl)(Cl)=O.BrC1C=CC([NH2:119])=C(N)C=1.[F-].[Cs+].NC1CCCCC1N.[C:131](O)(=O)[CH3:132].[CH:135]([NH2:137])=[NH:136]>[Cu](I)I>[NH:136]1[C:3]2[CH:2]=[CH:1][C:131]([N:40]3[C@@H:7]([C:8]4[CH:96]=[CH:105][C:11]([N:119]([CH:27]5[CH2:31][CH2:32]5)[CH:38]5[CH2:35][CH2:36]5)=[CH:10][CH:9]=4)[CH2:6][O:41][C:39]3=[O:49])=[CH:132][C:4]=2[N:137]=[CH:135]1

Participants

13

Reactant 11

HCID 46101,2-DiaminocyclohexaneHCID 8058HexaneHCID 24386Thionyl ChlorideHCID 25953Cesium fluorideHCID 160693Formamidine acetateHCID 3235934-Bromobenzene-1,2-diamineHCID 521297Tert-Butyl hypochloriteHCID 21713226HCID 21713226, compoundHCID 21983788HCID 21983788, compoundHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 178418339Butyllithium

Product 1

HCID 178519151HCID 178519151, compound

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

The compound was further synthesized according to method 5 starting from the product of step C (1.6 g, 7.96 mmol), 2.3M n-butyl lithium in hexane (6.19 mL, 14.92 mmol), triphenyl phosphonium methyl bromide (6.68 g, 15.92 mmol), T-butyl hypochloride (2 mL, 18.85 mmol), Boc carbamate (2.17 g, 18.60 mmol), (DHQ)2PHAL (240 mg, 0.309 mmol), potassium osmate dihydrate (90 mg, 0.247 mmol), Thionyl chloride (0.439 mL, 6.024 mmol), 4-bromo-1,2-diamino benzene (130 mg, 0.697 mmol), cesium fluoride (212 mg, 1.395 mmoles) and copper iodide (20 mg, 0.104 mmoles), 1,2-diaminocyclohexane (1 mL), formamidine acetate (23 mg, 0.219 mmoles). Yield: 0.03 g (0.6%). MS m/z 375.3 (M+H)+; 1H-NMR 400 MHz, CDCl3): δ 7.94 (s, 1H); 7.67 (s, 1H); 7.52 (s, 1H); 7.15 (d, 3H); 6.96 (d, 2H); 5.34 (q, 1H); 4.77 (t, 1H); 4.27 (q, 1H); 2.40-2.38 (t, 1H); 0.88-0.80 (m, 4H); 0.64-0.63 (m, 4H); HPLC (λ=214 nm, [A]: rt 14.39 min (95%).

Workup

  1. customThe compound was further synthesized
  2. customrt 14.39 min (95%)

Sources & evidence

ORD record
ord-ddb2b75b93ba40f8b288fe7c52c5f2a3
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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