Chloride → HCID 21105681, compound

HRID 2426696Notes

Reaction equation

HRID 2426696 reaction equation
C(N1CCC(C(O)=O)CC1)(OC(C)(C)C)=O.[Cl-].[CH3:18][N:19]([CH3:33])[CH:20]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28](NC)=[CH:27][CH:26]=2)[CH2:21]1.CN(C)C1CCN(C2C=C[C:44]([NH:47][C:48]([CH:50]3[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH2:51]3)=[O:49])=CC=2)C1>ClCCl.CN(C1C=CN=CC=1)C.C(N(CC)CC)C.N1C=CC=CC=1>[CH3:33][N:19]([CH3:18])[CH:20]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[CH:27][C:28]([CH2:44][NH:47][C:48]([CH:50]3[CH2:51][CH2:52][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:54][CH2:55]3)=[O:49])=[CH:29][CH:30]=2)[CH2:21]1

Participants

9

Reactant 4

HCID 312ChlorideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 21105538HCID 21105538, compoundHCID 21105680HCID 21105680, compound

Product 1

HCID 21105681HCID 21105681, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of N-Boc-piperidine-4-carboxylic acid (550 mg) and pyridine (0.47 ml) in dichloromethane (15 ml) was mixed with thinoyl chloride (0.21 ml) and, after 30 minutes, a solution of dimethyl[1-(4-methylaminophenyl)pyrrolidin-3-yl]amine (0.5 g), triethylamine (1.17 ml), DMAP (0.44 g) and dichloromethane (10 ml) was added dropwise. After 16 hours, the mixture was diluted with dichloromethane, washed with water and saturated brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (7N in methanol)). This resulted in the product with the molecular weight of 430.60 (C24H38N4O3); MS (ESI): 431 (M+H+). tert-Butyl 4-{[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]carbamoyl}piperidin-1-carboxylate can be prepared analogously.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (7N in methanol))
  5. customThis resulted in the product with the molecular weight of 430.60 (C24H38N4O3)

Sources & evidence

ORD record
ord-79c45775a8b84f44ae69c7b39c42fb28
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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