Triethylamine → N-[(3R)-6-(4-Hydroxyphenyl)-2-oxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

HRID 493664

Reaction equation

HRID 493664 reaction equation
C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH2:12][NH:11][C:10]1=[O:23].Cl[C:25](OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].Cl.Cl.[O:39]=[C:40]1[NH:48][C:43]2=[N:44][CH:45]=[CH:46][CH:47]=[C:42]2[N:41]1[CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O1CCCC1>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]2[CH2:12][NH:11][C:10](=[O:23])[C@H:9]([NH:8][C:25]([N:52]3[CH2:53][CH2:54][CH:49]([N:41]4[C:42]5[C:43](=[N:44][CH:45]=[CH:46][CH:47]=5)[NH:48][C:40]4=[O:39])[CH2:50][CH2:51]3)=[O:26])[CH2:15][CH2:14]2)=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 60037861(3R)-3-Amino-6-(4-hydroxyphenyl)azepan-2-one

Product 1

HCID 23656587N-[(3R)-6-(4-Hydroxyphenyl)-2-oxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamideYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.009 mL, 0.091 mmol) was added to a solution of (3R)-3-amino-6-(4-hydroxyphenyl)azepan-2-one (10 mg, 0.045 mmol) and 4-nitrophenyl chloroformate (18 mg, 0.091 mmol) in N,N-dimethylformamide (0.2 mL) and tetrahydrofuran (0.2 mL) at 0° C. After 1 h, 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (26 mg, 0.091 mmol) and diisopropylethylamine (0.032 mL, 0.182 mmol) were added and the mixture was allowed to warm to ambient temperature. After 18 h, the mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound (7 mg). MS 465.2243 (M+1).

Workup

  1. waitAfter 18 h
  2. customthe mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-0a0848e3a98f4443b2a7eacc55116fe0
Source dataset
uspto-grants-2009_05
Patent number
US07534784B2

Linked notes

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