Diisopropylethylamine → 2-[2-(4'-Chloro-4-methoxy-biphen-2-yl)-quinolin-6-yl]-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid Ethyl Ester

HRID 1788553Notes

Reaction equation

HRID 1788553 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]2[C:11]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17](C(O)=O)[CH:18]=4)[N:13]=3)=[CH:10][C:9]([O:25][CH3:26])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:62]([O:64][C:65]([C:67]1[CH:68]=[C:69]2[N:75]=[C:74](C3C=C4C(=CC=3)N=C(C3C=CC=CC=3Br)C=C4)[N:73]([CH:93]3[CH2:98][CH2:97][CH2:96][CH2:95][CH2:94]3)[C:70]2=[N:71][CH:72]=1)=[O:66])[CH3:63]>CN(C=O)C.CC(O)=O>[CH2:62]([O:64][C:65]([C:67]1[CH:68]=[C:69]2[N:75]=[C:74]([C:17]3[CH:18]=[C:19]4[C:14](=[CH:15][CH:16]=3)[N:13]=[C:12]([C:11]3[C:6]([C:5]5[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=5)=[CH:7][CH:8]=[C:9]([O:25][CH3:26])[CH:10]=3)[CH:21]=[CH:20]4)[N:73]([CH:93]3[CH2:98][CH2:97][CH2:96][CH2:95][CH2:94]3)[C:70]2=[N:71][CH:72]=1)=[O:66])[CH3:63]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 689192122-[2-(2-Bromo-phenyl)-quinolin-6-yl]-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylic Acid Ethyl EsterHCID 860273132-(4'-Chloro-4-methoxy-biphen-2-yl)-quinoline-6-carboxylic acid

Product 1

HCID 1317273792-[2-(4'-Chloro-4-methoxy-biphen-2-yl)-quinolin-6-yl]-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid Ethyl EsterYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The amine was reacted with Compound 525c (0.314 g, 0.805 mmol) in the presence of HBTU (0.32 g, 0.844 mmol) and DIEA (0.47 mL, 2.68 mmol) in DMF (10 mL), followed cyclization in AcOH (10 mL) according to procedure (2) and (3) in the preparation of Compound 477d. Separation by RP HPLC (from 20% of buffer B to 99% of buffer B) gave the title intermediate (0.19 g, 40%).

Workup

  1. customSeparation by RP HPLC (from 20% of buffer B to 99% of buffer B)

Sources & evidence

ORD record
ord-0a2f227c2a164f239c7c766c164959dc
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

Loading…