Triethylamine → HCID 18399312, compound

HRID 1019397Notes

Reaction equation

HRID 1019397 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([OH:43])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(Cl)(O[C:56](=[O:62])OC(Cl)(Cl)Cl)Cl.[CH3:64][N:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([O:43][C:56]([N:68]4[CH2:69][CH2:70][N:65]([CH3:64])[CH2:66][CH2:67]4)=[O:62])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 531671-MethylpiperazineHCID 94429TriphosgeneHCID 18399114HCID 18399114, compound

Product 1

HCID 18399312HCID 18399312, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of the compound obtained in Example 5 (100 mg) and triethylamine (50 mg) in chloroform (10 ml) is cooled to −10° C., and thereto is added dropwise a solution of triphosgene (49 mg) in chloroform. The mixture is warmed to room temperature, and the mixture is stirred for 30 minutes. To the mixture is added a solution of N-methylpiperazine (50 mg) and triethylamine (17 mg) in chloroform, and the mixture is further stirred for two hours. After the reaction is complete, the reaction mixture is washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 2[4-(tert-butoxycarbonylamino)phenyl]-6-methoxy-3-methoxycarbonyl-7-(4-methylpiperazinylcarbonyloxy)-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (73 mg) as listed in Table 20.

Workup

  1. stirringthe mixture is further stirred for two hours
  2. washthe reaction mixture is washed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-8a5a6df550f24f12a0c97fbab162f9f6
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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