Dimethylamine, hydrochloride → HCID 53378978, compound

HRID 2360981Notes

Reaction equation

HRID 2360981 reaction equation
C(OC([NH:8][CH:9]([CH2:37][C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)[C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH2:27][C:28]2[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=2)([C:18](=[O:26])[NH:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.Cl.[CH3:44][NH:45][CH3:46].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:20]1([NH:19][C:18]([C:15]2([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([C:32](=[O:33])[N:45]([CH3:46])[CH3:44])=[CH:35][CH:36]=3)[CH2:16][CH2:17][N:12]([C:10](=[O:11])[C@@H:9]([NH2:8])[CH2:37][C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)[CH2:13][CH2:14]2)=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67384315HCID 67384315, compound

Product 1

HCID 53378978HCID 53378978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[1-(2-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl)-4-cyclohexylcarbamoyl-piperidin-4-ylmethyl]-benzoic acid (0.201 mmol; 0.12 g) in DMF (1.5 mL) was added N,N-dimethylamine hydrochloride (0.241 mmol; 0.02 g), N,N-diisopropyl-N-ethylamine (0.502 mmol; 0.089 mL) and HBTU (0.241 mmol; 0.091 g), and the resulting mixture was stirred at room temperature overnight. The mixture was then purified via reverse phase HPLC and the desired fractions were combined and lyophilized. The resulting residue was dissolved in a 4N HCl solution in 1,4-dioxane (3 mL) and the resulting solution was stirred for 5 hours at room temperature and evaporated. The residue was triturated with diethyl ether and dried under vacuum to yield 1-(2-(S)-amino-3-thiophen-2-yl-propionyl)-4-(4-dimethylcarbamoyl-benzyl)-piperidine-4-carboxylic acid cyclohexylamide as a hydrochloride salt.

Workup

  1. customThe mixture was then purified via reverse phase HPLC
  2. dissolutionThe resulting residue was dissolved in a 4N HCl solution in 1,4-dioxane (3 mL)
  3. stirringthe resulting solution was stirred for 5 hours at room temperature
  4. customevaporated
  5. customThe residue was triturated with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-edd7a2781ef242908c1dba6728d4e147
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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