1,2-Diaminocyclohexane → HCID 178519151, compound
Reaction equation
C(=O)(O[C:4]([O:6][C:7]([CH3:10])(C)C)=[O:5])N.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H]([C:58]4[CH:67]=[CH:66][N:65]=[C:64]5[C:59]=4[CH:60]=[C:61](OC)[CH:62]=[CH:63]5)[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.Br[C:75]1[CH:80]=[CH:79][C:78](N)=[C:77]([NH2:82])[CH:76]=1.[F-].[Cs+].N[CH:86]1[CH2:91][CH2:90]CCC1N.C(O)(=O)C.[CH:97]([NH2:99])=[NH:98]>[Cu](I)I>[NH:98]1[C:80]2[CH:75]=[CH:76][C:77]([N:82]3[C@@H:10]([C:61]4[CH:60]=[CH:59][C:64]([N:65]([CH:66]5[CH2:67][CH2:58]5)[CH:90]5[CH2:91][CH2:86]5)=[CH:63][CH:62]=4)[CH2:7][O:6][C:4]3=[O:5])=[CH:78][C:79]=2[N:99]=[CH:97]1Participants
9
Reactant 7
HCID 46101,2-Diaminocyclohexane
HCID 24386Thionyl Chloride
HCID 25953Cesium fluoride
HCID 160693Formamidine acetate
HCID 3235934-Bromobenzene-1,2-diamine
HCID 21983788HCID 21983788, compound
HCID 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)phthalazineProduct 1
Reagents, catalysts & solvents 1
Procedure
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
- customrt 14.39 min (95%)
Sources & evidence
- ORD record
- ord-fa2fae8917514a3a98f18e4c00419512
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486940B2
Reaction notes
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