Triethylamine → HCID 58362578, compound

HRID 2361482Notes

Reaction equation

HRID 2361482 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][C:14](NC2C=CC(N)=CC=2)=[CH:13][CH:12]=1.Cl.Cl.N1C2C(=CC=CC=2)C=[CH:29][C:28]=1C1C=CC(N)=CC=1.C(OC([NH:51]C1C=CC(B(O)O)=CC=1)=O)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:16][C:15]1[CH:14]=[CH:13][C:12]([NH2:51])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3613184(4-Boc-Aminophenyl)Boronic AcidHCID 58362609HCID 58362609, compoundHCID 66700259HCID 66700259, compound

Product 1

HCID 58362578HCID 58362578, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(4-(Quinolin-2-yl)phenyl)benzene-1,4-diamine *3TFA: T447 To a solution of 4-(quinolin-2-yl)aniline dihydrochloride (7.6 mg, 0.026 mmol) in DCM (1.0 mL) was added 4-(tert-butoxycarbonylamino)phenylboronic acid (12.4 mg, 0.052 mmol), Cu(OAc)2 (4.8 mg, 0.026 mmol) and triethylamine (0.036 mL, 0.26 mmol). The mixture was stirred at room temperature for 3 hrs. LCMS showed that the desired product was formed. To the mixture was added 4 N HCl in dioxane (1.0 mL) and stirred for another hour. The mixture was concentrated in vacuo and purified by HPLC (acetonitrile/water) to give T447 as a brown solid (4.3 mg, 25%). 1H NMR (400 MHz, CD3OD): δ 8.77 (d, J=8.8 Hz, 1H), 8.16 (m, 2H), 8.10 (d, J=8.4 Hz, 1H), 8.01 (m, 2H), 7.96 (m, 1H), 7.73 (m, 1H), 7.21-729 (m, 6H); MS (ESI): 312 (M+H+).

Sources & evidence

ORD record
ord-698103b030f44f888276941c7f6b729f
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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