Tetrahydrofuran → Hydrochloric Acid

HRID 1599009Notes

Reaction equation

HRID 1599009 reaction equation
[NH2:1][C:2]1[C:3]([O:28][CH3:29])=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:24][CH2:23][C:16]3([NH:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])[CH2:15][CH2:14]2)[CH:7]=1.[F:30][C:31]([F:48])([F:47])[C:32]1[N:36]([CH3:37])[N:35]=[C:34]([C:38]2[CH:42]=[CH:41][S:40][C:39]=2[S:43]([Cl:46])(=[O:45])=[O:44])[CH:33]=1.C1COCC1.CN1CCCC1=O>C(O)C.CCOCC>[ClH:46].[ClH:46].[O:21]=[C:19]1[NH:18][C:17](=[O:22])[C:16]2([CH2:15][CH2:14][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:6]3[C:5]([O:26][CH3:27])=[CH:4][C:3]([O:28][CH3:29])=[C:2]([NH:1][S:43]([C:39]4[S:40][CH:41]=[CH:42][C:38]=4[C:34]4[CH:33]=[C:32]([C:31]([F:30])([F:47])[F:48])[N:36]([CH3:37])[N:35]=4)(=[O:44])=[O:45])[CH:7]=3)=[O:25])[CH2:24][CH2:23]2)[NH:20]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 18931306HCID 18931306, compoundHCID 18931437HCID 18931437, compound

Product 2

HCID 313Hydrochloric AcidHCID 18931244HCID 18931244, compound

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

A mixture of 8-[5-(5-amino-2,4-dimethoxyphenyl)-5-oxopentyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione (202 mg, 0.5 mmol), prepared as in Example 21, 3-(5-trifluoromethyl-1-methylpyrazol-3-yl)-2-thiophenesulfonyl chloride. (200 mg, 0.6 mmol) and THF (1 mL) and N-methyl-2-pyrrolidinone (1 mL) was stirred 16 hours at approximately 25° C. The mixture was purified by flash chromatography eluting first with methylene chloride and then with methylene chloride/methanol+ammonium hydroxide (9:1). The purified product was recrystallized from ethanol and then from a solution of hydrogen chloride in ethanol/ether to give N-{5-[5-(2,4-dioxo-1,3,8-triazaspiro[4.5]dec-8-yl)pentanoyl]-2,4-dimethoxyphenyl}-3-(5-trifluoromethyl-1-methylpyrazol-3-yl)-2-thiophenesulfonamide hydrochloride (94 mg, 0.13 mmol), m.p. 162°-170° C.

Workup

  1. customThe mixture was purified by flash chromatography
  2. washeluting first with methylene chloride
  3. customThe purified product was recrystallized from ethanol

Sources & evidence

ORD record
ord-026ce6a1365344d190a3c2139b6040d9
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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