Triethylamine → HCID 10169512, compound

HRID 1278606Notes

Reaction equation

HRID 1278606 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:49])[CH2:19][C:20]3[NH:21][C:22]([CH2:42][CH2:43][C:44]4[S:45][CH:46]=[CH:47][N:48]=4)=[C:23]([C:38]([O:40][CH3:41])=[O:39])[CH:24]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:37])[C:25]=3[C:26]([O:28][CH3:29])=[O:27])[CH2:14][CH2:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:50][S:51](Cl)(=[O:53])=[O:52].C(N(CC)CC)C>ClCCl>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[CH:24]1[C:23]([C:38]([O:40][CH3:41])=[O:39])=[C:22]([CH2:42][CH2:43][C:44]2[S:45][CH:46]=[CH:47][N:48]=2)[NH:21][C:20]([CH2:19][C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:5]3([CH2:4][NH:3][S:51]([CH3:50])(=[O:53])=[O:52])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[CH2:13][CH2:14]2)=[O:49])=[C:25]1[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18430896HCID 18430896, compound

Product 1

HCID 10169512HCID 10169512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of dimethyl 2-[2-[4-[[1-(aminomethyl)cyclohexyl]methyl]-1-piperazinyl]-2-oxoethyl]-4-(2,6-dichlorophenyl)-6-[2-(1,3-thiazol-2-yl)ethyl]-1,4-dihydro-3,5-pyridinedicarboxylate dihydrochloride (230 mg/0.28 mmol) methansulfonylchloride (0.2 ml/2.5 mmol) and triethylamine (0.5 ml/3.5 mmol) in dichloromethane (5.0 ml) was stirred for 5 hours at ambient temperature. The mixture was diluted with dichloromethane (50 ml), and then washed with water (10 ml) and brine (10 ml) successively. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel/200-350 mesh/20 g/dichloromethane) to give a yellow film (122 mg/55%).

Workup

  1. washwashed with water (10 ml) and brine (10 ml) successively
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (NH2 gel/200-350 mesh/20 g/dichloromethane)
  6. customto give a yellow film (122 mg/55%)

Sources & evidence

ORD record
ord-2b6369eaed064556938a54bfd7b1f0d2
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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