Ammonia → 8-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithiaoctanoic acid

HRID 22593

Reaction equation

HRID 22593 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][S:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30]([OH:32])=O)[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[I-].ClC1C=CC=C[N+:36]=1C.C(N(CC)CC)C.N>ClCCl.C(#N)C.CCOCC>[C:30]([CH2:29][CH2:28][S:27][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([S:13][CH2:12][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:32])[NH2:36]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 104139205-(3-(7-Chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithianonanedioic acid

Product 1

HCID 199305208-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithiaoctanoic acid

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To 500 mg of diacid (Example 20, Step 4) in dichloromethane (39 mL) and acetonitrile (9.9 mL) at 0° C. was added 2-chloro-1-methylpyridinium iodide (315 mg). After 15 min triethylamine (170 μL) and 10 mL of a saturated solution of ammonia in ether were added. The solution was stirred 1 hr at room temperature then it was washed with acidified 25% ammonium acetate, extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. Purification by chromatography afforded the title compound.

Workup

  1. washit was washed
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-32fdaef34b434ee89b0bff3ed1e90296
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Linked notes

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