Hydrochloric Acid → HCID 21849923, compound

HRID 617816Notes

Reaction equation

HRID 617816 reaction equation
CN(C)CCNC(C1C=CC=C2C=1NC1C=CC3C=C(NS(C4C=CC(C)=CC=4)(=O)=O)C=CC=3C2=1)=O.[H-].[Na+].[Cl:39]C(OCC)=O.[CH3:45][N:46]([CH3:87])[CH2:47][CH2:48][N:49]1[C:84](=[O:85])[C:53]2[CH:54]=[CH:55][CH:56]=[C:57]3[C:58]4[C:59]5[CH:67]=[CH:66][C:65]([N:68](C(OCC)=O)[S:69]([C:72]6[CH:77]=[CH:76][C:75]([CH3:78])=[CH:74][CH:73]=6)(=[O:71])=[O:70])=[CH:64][C:60]=5[CH:61]=[CH:62][C:63]=4[N:51]([C:52]=23)[C:50]1=[O:86].[OH-].[Na+].Cl>CN(C)C=O.CO.O1CCCC1>[ClH:39].[CH3:87][N:46]([CH3:45])[CH2:47][CH2:48][N:49]1[C:84](=[O:85])[C:53]2[CH:54]=[CH:55][CH:56]=[C:57]3[C:58]4[C:59]5[CH:67]=[CH:66][C:65]([NH:68][S:69]([C:72]6[CH:73]=[CH:74][C:75]([CH3:78])=[CH:76][CH:77]=6)(=[O:71])=[O:70])=[CH:64][C:60]=5[CH:61]=[CH:62][C:63]=4[N:51]([C:52]=23)[C:50]1=[O:86]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 21849960HCID 21849960, compoundHCID 69866465HCID 69866465, compound

Product 1

HCID 21849923HCID 21849923, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Production Example 24 was treated in the same manner as the one of Production Example 3 to thereby give N-[2-(dimethylamino)ethyl]-3-(4-methylbenzenesulfonamido)-7H-benzo[c]carbazole-8-carboxamide. Then this product was reacted with sodium hydride and ethyl chloroformate in dimethylformamide under ice-cooling to thereby give 5-[2-(dimethylamino)ethyl]-11-(N-etoxycarbonyl-4-methylbenzenesulfonamido)-4H-benzo[c]pyrimido[5,6,1-jk]carbazole-4,6(5H)-dione. Next, this product was treated with a 1 N aqueous solution of sodium hydroxide in a mixture of methanol with tetrahydrofuran (1:1) and then converted into the hydrochloride in a conventional manner followed by recrystallization from ethanol to thereby give the title compound.

Workup

  1. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-c2b37eda7e3f4132924fc2ff727e43cb
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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