Diisopropylethylamine → HCID 53378984, compound

HRID 2360987Notes

Reaction equation

HRID 2360987 reaction equation
Cl.[CH:2]1([CH2:8][NH:9][C:10]([C:12]2([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][CH:20]=3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(OC([NH:35][C@@H:36]([CH2:40][C:41]1[S:42][CH:43]=[CH:44][CH:45]=1)[C:37](O)=[O:38])=O)(C)(C)C.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:2]1([CH2:8][NH:9][C:10]([C:12]2([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][CH:20]=3)[CH2:13][CH2:14][N:15]([C:37](=[O:38])[C@@H:36]([NH2:35])[CH2:40][C:41]3[S:42][CH:43]=[CH:44][CH:45]=3)[CH2:16][CH2:17]2)=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27344843-(Thien-2-yl)-L-alanine, N-BOC protectedHCID 67384462HCID 67384462, compound

Product 1

HCID 53378984HCID 53378984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-carbamoylbenzyl)-piperidine-4-carboxylic acid cyclohexylmethylamide hydrochloride (0.584 mmol; 0.23 g) in DMF (5 mL) was added (S)-2-tert-butoxycarbonylamino-3-thiophen-2-yl-propionic acid (0.642 mmol; 0.174 g), N,N-diisopropyl-N-ethylamine (2.335 mmol; 0.413 mL) and HBTU (0.701 mmol; 0.266 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 THF (5 mL) and a 4N HCl solution in 1,4-dioxane (10 mL) was added. 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-carbamoylbenzyl)-piperidine-4-carboxylic acid cyclohexylmethylamide as a hydrochloride salt.

Workup

  1. customThe mixture was then purified via reverse phase HPLC
  2. dissolutionThe resulting residue was dissolved in THF (5 mL)
  3. additiona 4N HCl solution in 1,4-dioxane (10 mL) was added
  4. stirringThe resulting solution was stirred for 5 hours at room temperature
  5. customevaporated
  6. customThe residue was triturated with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-1cb79015aae14b1b86049886b408c3f2
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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