Diisopropylethylamine → HCID 86601613, compound

HRID 1768253Notes

Reaction equation

HRID 1768253 reaction equation
C([N:3]=[C:4](OC1C=CC=CC=1)[NH:5][C@@H:6]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[CH2:9][N:8]([CH2:21][CH3:22])[C:7]1=[O:23])#N.Cl.Cl.[O:33]=[C:34]1[NH:42][C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:36]2[N:35]1[CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.[CH:49]([N:52](CC)C(C)C)(C)C>C(O)CCCC>[C:49]([N:5]([C@@H:6]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[CH2:9][N:8]([CH2:21][CH3:22])[C:7]1=[O:23])[C:4]([N:46]1[CH2:47][CH2:48][CH:43]([N:35]2[C:36]3[C:37](=[N:38][CH:39]=[CH:40][CH:41]=3)[NH:42][C:34]2=[O:33])[CH2:44][CH2:45]1)=[NH:3])#[N:52]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 178462635HCID 178462635, compound

Product 1

HCID 86601613HCID 86601613, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A solution of phenyl N′-cyano-N-[(3R,6S)-6-(2,3-difluorophenyl)-1-ethyl-2-oxoazepan-3-yl]imidocarbamate (166 mg, 0.402 mmol) and 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (116 mg, 0.402 mmol), in 1-pentanol (10 mL) was treated with N,N-diisopropylethylamine (52 mg, 0.402 mmol). This mixture was heated to reflux for 24 h. Concentration and purification by silica gel chromatography (0%→10% methanol/dichloromethane) followed by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (10 mg). MS 537.5 (M+1).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationConcentration and purification by silica gel chromatography (0%→10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a18c98e728f74e8e9ced38ec7aeb396d
Source dataset
uspto-grants-2007_06
Patent number
US07235545B2

Reaction notes

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