Triethylamine → HCID 71547892, compound

HRID 1184556Notes

Reaction equation

HRID 1184556 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9](Cl)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[NH2:13][C@@H:14]1[CH2:29][N:17]2[CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][C@@H:16]2[CH2:15]1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:13][C@@H:14]2[CH2:29][N:17]3[CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:21][C@@H:16]3[CH2:15]2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 43810901HCID 43810901, compound

Product 1

HCID 71547892HCID 71547892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chlorophenyl)methanesulfonyl chloride (1.125 g, 5 mmol) in dichloromethane (10 mL) was added (7S,8aS)-tert-butyl 7-aminohexahydro-pyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (1.400 g, 5.80 mmol) followed by triethylamine (0.758 g, 7.5 mmol). The mixture was stirred at room temperature overnight, and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate) to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.25 (m, 1H), 1.39 (s, 9 H), 1.80 (m, 1 H), 1.95 (m, 1 H), 2.07-2.23 (m, 2 H), 2.89 (m, 3 H), 2.75-3.98 (m, 3 H), 4.32 (s, 2H), 7.43 (m, 5H). MS (ESI) m/z 431 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-6464a496451240638f22858bd235f874
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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