Hydrochloric Acid → HCID 89077752, compound

HRID 1946212Notes

Reaction equation

HRID 1946212 reaction equation
[CH3:1][C:2]1([CH3:28])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O-:13])=O)[CH:9]=2)[N+:4]2[CH:14]=[CH:15][C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH3:27])[CH:19]=3)=[CH:17][C:3]1=2.[ClH:29].[C:30]([N:37]1[CH:41]=[CH:40]N=[CH:38]1)(N1C=CN=C1)=O.Cl.Cl.[NH2:44][CH2:45][CH2:46][S:47][S:48][CH2:49][CH2:50][NH2:51]>CN1CCCC1=O.O1CCOCC1.C(OCC)C.C(N(C(C)C)CC)(C)C.CC(C)=O>[Cl-:29].[Cl-:29].[S:47]([CH2:46][CH2:45][NH:44][C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N+:4]1[CH:14]=[CH:15][C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH3:27])[CH:19]=3)=[CH:17][C:3]=1[C:2]2([CH3:1])[CH3:28])=[O:13])[S:48][CH2:49][CH2:50][NH:51][C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N+:4]1[CH:14]=[CH:15][C:16]([C:40]3[C:25]4[C:38](=[CH:23][CH:22]=[CH:21][CH:26]=4)[N:37]([CH3:30])[CH:41]=3)=[CH:17][C:3]=1[C:2]2([CH3:28])[CH3:1])=[O:13]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 5941Cystamine DihydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 68743932HCID 68743932, compound

Product 1

HCID 89077752HCID 89077752, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

10,10-dimethyl-8-(1-methyl-1H-indol-3-yl)-10H-pyrido-[1,2-a]indolium-2-carboxylate 0.37 g was solubilized in 5 mL N-methylpyrrolidinone (NMP), a solution of HCl in dry dioxane and diethyl ether (1 mL; 1N; 1:3) was added and 1,1′-carbonyldiimidazole (320 mg) was progressively added. After 3 h, 200 mg of cystamine dihyrochloride in mL diisopropylethylamine (DIPEA) were added to the mixture. After 24 h, the reaction mixture was poured in 100 mL acetone. The resulting solid was filtered, washed with acetone and dried under vacuum (340 mg, yellow powder). Analyses were in accordance with the expected structure.

Workup

  1. waitAfter 24 h
  2. filtrationThe resulting solid was filtered
  3. washwashed with acetone
  4. customdried under vacuum (340 mg, yellow powder)

Sources & evidence

ORD record
ord-38778b693abf47bc90b7d54082ae4183
Source dataset
uspto-grants-2013_03
Patent number
US08398722B2

Reaction notes

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