Dimethylamine, hydrochloride → HCID 9851312, compound

HRID 411288Notes

Reaction equation

HRID 411288 reaction equation
[CH2:1]([N:12]1[CH:17]=[C:16]([CH2:18][C:19]2[CH:20]=[N:21][C:22](=[O:29])[N:23]([CH2:25][C:26](O)=[O:27])[CH:24]=2)[C:15](=[O:30])[N:14]=[C:13]1[S:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl.[CH3:41][NH:42][CH3:43].C(N(C(C)C)CC)(C)C.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CO.C(=O)([O-])[O-].[K+].[K+]>[CH2:1]([N:12]1[CH:17]=[C:16]([CH2:18][C:19]2[CH:20]=[N:21][C:22](=[O:29])[N:23]([CH2:25][C:26]([N:42]([CH3:43])[CH3:41])=[O:27])[CH:24]=2)[C:15](=[O:30])[N:14]=[C:13]1[S:31][CH2:32][C:33]1[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

9

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9893934HCID 9893934, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 9851312HCID 9851312, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 1-undecyl-2-(4-fluorobenzyl)thio-5-(1-(carboxymethyl)-2-oxopyrimid-5-ylmethyl)pyrimidin-4-one, dimethylamine hydrochloride (0.02 g), diisopropylethylamine (0.045 ml), hydroxybenzotriazole (0.005 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.045 g) in dry methylene chloride were stirred together for 24 h and diluted with 3% methanol in methylene chloride and 5% aqueous potassium carbonate. The organic layer was added directly to a SepPak cartridge (SiO2, 10 g) and eluted with 0-20% methanol in ethyl acetate to give the desired product (0.085 g). 1H-NMR (CDCl3) δ0.8-0.95 (3H,m), 1.15-1.4 (16H,m), 1.6-1.85 (2H,m), 2.98 (3H,s), 3.13 (3H,s), 3.49 (2H,s), 3.77 (2H,t), 4.46 (2H,s), 4.74 (2H,s), 6.9-7.1 (2H,m), 7.14 (1H,s), 7.3-7.45 (2H,m), 7.78 (1H,bd), 8.49 (1H,bd); MS (APCI+) found (M+1)=584; C31H42FN5O3S requires 583.

Workup

  1. additionThe organic layer was added directly to a SepPak cartridge (SiO2, 10 g)
  2. washeluted with 0-20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-a75b1b6d87a94f42a194c6dde09ef78d
Source dataset
uspto-grants-2003_05
Patent number
US06559155B1

Reaction notes

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