Sodium Hydroxide → HCID 178459270, compound

HRID 2199526Notes

Reaction equation

HRID 2199526 reaction equation
[OH-].[Na+].Cl.[CH3:4][N:5]([CH3:12])[C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[NH:7].[CH:13]1([N:19]([C@H:33]2[CH2:38][CH2:37][C@H:36]([O:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:34]2)[C:20](=[O:32])[NH:21][C:22]2[S:23][C:24]([S:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:25][N:26]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O.C(O)C>[CH3:4][N:5]([CH3:12])[C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[NH:7].[CH:13]1([N:19]([C@H:33]2[CH2:34][CH2:35][C@H:36]([O:39][CH2:40][CH2:41][CH3:42])[CH2:37][CH2:38]2)[C:20](=[O:32])[NH:21][C:22]2[S:23][C:24]([S:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:25][N:26]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 178459270HCID 178459270, compoundHCID 178484384HCID 178484384, compound

Product 2

HCID 178459270HCID 178459270, compoundHCID 178484382HCID 178484382, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

NaOH (0.8 g) was dissolved in water (20 mL) and then cooled to room temperature. 1,1-dimethylbiguanide hydrochloride (3.6 g) was then added and stirred to obtain a clear solution. The resulting solution was added to a suspension of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid (UD1) (9.1 g) in ethanol (80 mL) with stirring at room temperature. The reaction mixture turned clear in 3-5 minutes. The volatiles were evaporated to obtain a syrup, which was dissolved in ethanol (100 mL) and then concentrated. White precipitate was obtained when about 50 mL of volatiles were removed by evaporation. This precipitate was filtered and dried under reduced pressure to obtain a 1,1-dimethylbiguanide salt of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid. The 1H NMR spectrum recorded in DMSO-d6 indicated the precipitate contained {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid and 1,1-dimethylbiguanide in 1:1 ratio. 1H NMR (400 MHz, DMSO-d6): δ 0.85 (t, 3H), 1.05-2.15 (m, 20H), 2.92 (s, 6H), 3.18 (m, 1H), 3.30 (s, 2H), 3.34 (t, 2H), 3.45 (br, 1H), 7.1 (br, NH protons), 7.21 (s, 1H) ppm.

Workup

  1. customto obtain a clear solution
  2. stirringwith stirring at room temperature
  3. customThe volatiles were evaporated
  4. customto obtain a syrup, which
  5. concentrationconcentrated
  6. customWhite precipitate was obtained when about 50 mL of volatiles
  7. customwere removed by evaporation
  8. filtrationThis precipitate was filtered
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e5fcd84193b042fabf68c7840cbe970b
Source dataset
uspto-grants-2016_06
Patent number
US09359313B2

Reaction notes

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