Sodium Hydroxide → HCID 54150262, compound

HRID 1266347Notes

Reaction equation

HRID 1266347 reaction equation
C1(O[C:8](=[O:24])[NH:9][C:10]2[S:14][N:13]=[C:12]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:11]=2[C:21](=[O:23])[NH2:22])C=CC=CC=1.[NH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.[OH-].[Na+]>O1CCCC1>[CH2:16]([S:15][C:12]1[C:11]([C:21]([NH2:22])=[O:23])=[C:10]([NH:9][C:8]([NH:25][CH2:26][CH2:27][CH2:28][N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[O:24])[S:14][N:13]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 316701-PyrrolidinepropanamineHCID 68505538HCID 68505538, compound

Product 1

HCID 54150262HCID 54150262, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-carbamoyl-3-pentylsulfanyl-isothiazol-5-yl)-carbamic acid phenyl ester (0.10 g, 0.27 mmol) and 1 mL of tetrahydrofuran was added N-3-aminopropylpyrollidine (0.175 g, 1.4 mmol). After stirring for 72 hours at ambient temperature, the mixture was poured into 1M NaOH, extracted twice with ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated. Purification of the residue by radial chromatography (2 mm plate, 3% ethanol-CH2Cl2— 30% ethanol-CH2Cl2 containing 0.5% NH4OH), followed by concentration and trituration of the residue with ether-hexane afforded 0.076 g (78%) of 3-pentylsulfanyl-5-[3-(3-pyrrolidin-1-yl-propyl)-ureido]-isothiazole-4-carboxylic acid amide as a colorless solid 1H NMR (400 MHz, CDCl3) δ 7.57 (bs, 1H), 7.06 (bs, 2H), 3.35 (m, 2H), 3.26(m, 2H), 2.53 (t, 2H, J=6.8Hz), 2.47(m, 4H), 1.73 (m, 8H), 1.4-1.2 (m, 4H), 0.88 (t, 3H, J=7.2 Hz) ppm; MS (APCl, m/z): 400 [M+H]+.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by radial chromatography (2 mm plate, 3% ethanol-CH2Cl2— 30% ethanol-CH2Cl2 containing 0.5% NH4OH)
  6. concentrationfollowed by concentration and trituration of the residue with ether-hexane

Sources & evidence

ORD record
ord-2bcbb759ed41415a972e5cf25c137d1a
Source dataset
uspto-grants-2003_04
Patent number
US06548526B2

Reaction notes

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