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{1-[1-(4-Pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester → 1-Amino-cyclopropanecarboxylic acid [1-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropyl]-amide

HRID 1040511
Notes
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Reaction equation

HRID 1040511 reaction equation
C(OC(=O)[NH:10][C:11]1([C:14](=[O:31])[NH:15][C:16]2([C:19]3[CH:24]=[C:23]([CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH:22]=[CH:21][N:20]=3)[CH2:18][CH2:17]2)[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[N:26]1([CH2:25][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([C:16]3([NH:15][C:14]([C:11]4([NH2:10])[CH2:12][CH2:13]4)=[O:31])[CH2:17][CH2:18]3)[CH:24]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 58431218{1-[1-(4-Pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester

Product 1

HCID 584312021-Amino-cyclopropanecarboxylic acid [1-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropyl]-amideYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 100 mL one neck round bottom flask, {1-[1-(4-Pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester (67 mg, 0.154 mmol) was dissolved in MeOH (10 mL). 10 Wt. % Pd/C (15 mg) was then added. Nitrogen gas was bubbled through the suspension for 10 min. The reaction flask was evacuated and then filled with H2. This purging process was repeated twice and then the reaction was allowed to stir for 16 h under H2 (1 atm). The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to afford 39.3 mg of the title compound as a white solid.

Workup

  1. customNitrogen gas was bubbled through the suspension for 10 min
  2. customThe reaction flask was evacuated
  3. additionfilled with H2
  4. filtrationThe reaction mixture was filtered through celite
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-35bd872fe9dc496ea7199136ceaf7d91
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552205B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes