1,2-Diaminocyclohexane → HCID 178519088, compound

HRID 706333Notes

Reaction equation

HRID 706333 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Br-].C1([PH+]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)C2C=CC=CC=2)C=CC=CC=1.O1CCN(C2C[CH2:36][CH:35]([C:38]3[CH:45]=[CH:44][C:41](C=O)=[CH:40][CH:39]=3)CC2)CC1.ClO[C:48]([CH3:51])(C)C.[C:52](=[O:62])([O:54]C(OC(C)(C)C)=O)[NH2:53].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C([O:97][C@H:98](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H:99]4[N:104]5[CH2:105][C@H:106](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.S(Cl)(Cl)=O.NC1C=CC(Br)=C[C:127]=1[NH2:133].[F-].[Cs+].[NH2:136]C1CCCCC1N>[Cu](I)I.C(O)=O>[NH:136]1[C:3]2[CH:2]=[CH:1][C:48]([N:53]3[CH:35]([C:38]4[CH:39]=[CH:40][C:41]([CH:20]5[CH2:21][CH2:22][CH:23]([N:104]6[CH2:99][CH2:98][O:97][CH2:106][CH2:105]6)[CH2:24][CH2:25]5)=[CH:44][CH:45]=4)[CH2:36][O:54][C:52]3=[O:62])=[CH:51][C:4]=2[N:133]=[CH:127]1

Participants

13

Reactant 10

HCID 46101,2-DiaminocyclohexaneHCID 24386Thionyl ChlorideHCID 25953Cesium fluorideHCID 3235934-Bromobenzene-1,2-diamineHCID 517696Phosphine, triphenyl-, hydrobromideHCID 521297Tert-Butyl hypochloriteHCID 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 57488485HCID 57488485, compoundHCID 178418339Butyllithium

Product 1

HCID 178519088HCID 178519088, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 284Formic AcidSolvent

Procedure

The compound was synthesized according to method 5 starting from n-butyl lithium (2.3M in hexane; 3.66 mL, 7.32 mmol), tri phenyl phosphonium bromide (2.6 g, 7.32 mmol), 4-(4-morpholinocyclohexyl)benzaldehyde (1 g, 3.66 mmol), t-butyl hypochlorite (1.13 mL, 8.85 mmol), Boc carbamate (1.03 g, 8.85 mmol) 0.4M aqueous sodium hydroxide (360 mg in 10 mL), (DHQ)2PHAL (114 mg, mmol), potassium osmate dihydrate (40 mg, 0.12 mmol), thionyl chloride (0.6 mL, 8 mmol), 1,2-diamino-4-bromobenzene (160 mg, 0.84 mmol) and cesium fluoride (190 mg, 1.26 mmol), copper iodide (25 mg, 0.13 mmol) and 1,2-diaminocyclohexane (15 mg, 0.13 mmol), formic acid (10 mL). Yield: 40 mg (2.4%), MS m/z 447.4 (M+H)+; 1H-NMR (400 MHz, DMSO-d6): δ 12.38 (s, 1H); 8.15 (s, 1H); 7.60-7.16 (m, 6H); 5.69 (t, 1H); 4.8 (t, 1H); 4.13-4.10 (q, 1H); 3.57 (t, 4H); 2.56 (merged with DMSO, 1H); 2.33 (s, 4H); 2.11 (s, 1H); 1.91-1.67 (m, 5H); 1.45-1.38 (m, 4H), HPLC (λ=214 nm, [A]: rt 7.95 min (97.87%)

Workup

  1. customThe compound was synthesized
  2. customrt 7.95 min (97.87%)

Sources & evidence

ORD record
ord-d798076a06cc4d3f9165ab75b2a65f3d
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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