Hydrochloric Acid → HCID 59402504, compound

HRID 655775Notes

Reaction equation

HRID 655775 reaction equation
[Cl:1][C:2]1[C:3]([C:11]#[N:12])=[C:4]([C:8]([OH:10])=O)[NH:5][C:6]=1[CH3:7].[NH2:13][C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][C@@H:15]1[CH3:24].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.Cl>ClCCl>[Cl:1][C:2]1[C:3]([C:11]#[N:12])=[C:4]([C:8]([NH:13][C@@H:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][C@@H:15]2[CH3:24])=[O:10])[NH:5][C:6]=1[CH3:7]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58075083Methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate2×HCID 594025744-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid2×

Product 1

HCID 59402504HCID 59402504, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 16, 2.12 g, 0.02 mol) and methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate (Intermediate 37, 2.0 g, 0.02 mol) in dichloromethane (200 mL) was added HOBt (1.77 g, 0.02 mol) and N-methyl morpholine (3.8 mL, 0.03 mol) and then the mixture was stirred for 1 h at room temperature. EDC HCl (3.98 g, 0.0208 mol) was added to the reaction mixture and stirred at room temperature overnight. The reaction mixture was added to 2N hydrochloric acid (200 mL). The organic layer was washed with sodium bicarbonate (200 mL), water (250 mL), and brine. The organic layer was dried over anhydrous sodium sulphate, filtered, concentrated under vacuum to get methyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate 3.3 g (72%) as white solid.

Workup

  1. stirringstirred at room temperature overnight
  2. washThe organic layer was washed with sodium bicarbonate (200 mL), water (250 mL), and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3697475cfb5d493caaa689238d7b7ab5
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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