1,1'-Carbonyldiimidazole → HCID 86629525, compound

HRID 1711162Notes

Reaction equation

HRID 1711162 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].CCN(C(C)C)C(C)C.C1N=CN([C:19](N2C=NC=C2)=[O:20])C=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][CH2:40][C:41]2[CH:45]=[CH:44][S:43][CH:42]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C([O-])(O)=O.[Na+]>CC#N>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([N:39]([CH2:40][C:41]2[CH:45]=[CH:44][S:43][CH:42]=2)[C:19]([NH:4][O:2][CH3:3])=[O:20])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 5

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 63248157HCID 63248157, compound

Product 1

HCID 86629525HCID 86629525, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of methoxylamine hydrochloride (0.520 g, 6.25 mmol) in CH3CN (15 ml) was added DIPEA (1.09 ml, 6.25 mmol) followed by CDI (1.02 g, 6.25 mmol) and the reaction stirred at rt for 1.5 h after which a solution of the amine from above (0.880 g, 3.12 mmol) in CH3CN (10 ml) was added and the reaction stirred at 60° C. overnight. The solution was cooled, treated with saturated aqueous NaHCO3 (20 ml) and extracted with CH2Cl2 (3×15 ml). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v) gave 4-(3-methoxy-1-thiophen-3-ylmethyl-ureido)-piperidine-1-carboxylic acid tert-butyl ester as a white foam (0.95 g, 86%). 1H-NMR (CDCl3) δ 1.43 (s, 9H), 1.54 (m, 1H), 1.75 (d, 2H, J=9.0 Hz), 2.79 (br t, 1H), 3.65 (s, 3H), 4.17 (m, 2H), 4.27 (s, 2H), 6.96 (d, 1H, J=3.0 Hz), 7.08 (s, 1H), 7.11 (s, 1H), 7.36 (m, 1H).

Workup

  1. additionwas added
  2. temperatureThe solution was cooled
  3. extractionextracted with CH2Cl2 (3×15 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v)

Sources & evidence

ORD record
ord-c448840cbdcd4389be3dcc57dcdf5a86
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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