Diisopropylethylamine → HCID 67384736, compound

HRID 2360984Notes

Reaction equation

HRID 2360984 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:34][C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)([C:17](=[O:25])[NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:13][CH2:12]1)=[O:10])(C)(C)C.N1C=CC=CC=1S(Cl)(=O)=[O:48].C(N([CH:57]([CH3:59])C)CC)(C)C>ClCCCl>[CH:19]1([NH:18][C:17]([C:14]2([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:57](=[O:48])[CH3:59])=[CH:29][CH:28]=3)[CH2:13][CH2:12][N:11]([C:9](=[O:10])[CH:8]([NH2:7])[CH2:34][C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)[CH2:16][CH2:15]2)=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 67385076HCID 67385076, compound

Product 1

HCID 67384736HCID 67384736, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of {2-[4-(4-aminobenzyl)-4-cyclohexylcarbamoyl-piperidin-1-yl]-2-oxo-1-thiophen-2-ylmethyl-ethyl}-carbamic acid tert-butyl ester (0.352 mmol; 0.2 g) in 1,2-dichloroethane (5 mL) was added pyridine-2-sulfonyl chloride (0.422 mmol; 0.075 g) and N,N-diisopropyl-N-ethylamine (0.703 mmol; 0.123 mL) and the resulting solution was stirred for 3 hours at room temperature. The resulting mixture was evaporated and the residue was purified via reverse phase HPLC. The desired fractions were combined and lyophilized. The residue was dissolved in tetrahydrofuran (10 mL) and a 4N HCl in 1,4-dioxane solution (15 mL), and the resulting mixture was stirred for 6 hours at room temperature and evaporated. The residue was triturated with diethyl ether and dried under vacuum to yield 4-(4-acetylaminobenzyl)-1-(2-amino-3-thiophen-2-yl-propionyl)-piperidine-4-carboxylic acid cyclohexylamide as a hydrochloride salt.

Workup

  1. customThe resulting mixture was evaporated
  2. customthe residue was purified via reverse phase HPLC
  3. dissolutionThe residue was dissolved in tetrahydrofuran (10 mL)
  4. stirringa 4N HCl in 1,4-dioxane solution (15 mL), and the resulting mixture was stirred for 6 hours at room temperature
  5. customevaporated
  6. customThe residue was triturated with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ded068bcd20c42988249214adbc1cb5b
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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