HCID 15257492, compound → HCID 13851179, compound

HRID 978448Notes

Reaction equation

HRID 978448 reaction equation
C(O[C:4]([NH:6][C:7]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:8]=1[C:9]([O:11]CC)=O)=[O:5])C.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][NH2:36])[CH2:30][CH2:29]2)=[CH:20]1>>[OH:18][C:15]1[CH:14]=[C:8]2[C:7](=[CH:17][CH:16]=1)[NH:6][C:4](=[O:5])[N:36]([CH2:35][CH2:34][N:31]1[CH2:30][CH2:29][CH:28]([C:21]3[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:19][CH:20]=3)[CH2:33][CH2:32]1)[C:9]2=[O:11]

Participants

3

Reactant 2

HCID 15257492HCID 15257492, compoundHCID 20202890HCID 20202890, compound

Product 1

HCID 13851179HCID 13851179, compoundYield 70%

Conditions

Temperature
200 °C

Procedure

A mixture of 12.5 parts of ethyl 2-(ethoxycarbonylamino)-5-hydroxybenzoate and 12 parts of 4-(1H-indol-3-yl)-1-piperidineethanamine was stirred in an oil bath at about 200° C. and under nitrogen atmosphere. The formed ethanol was distilled off. The whole was cooled and the solid product was crystallized from a mixture of ethanol and acetonitrile. The product was filtered off and dried, yielding 14.5 parts (70%) of 6-hydroxy-3-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione; mp. 258.2° C. (compound 1).

Workup

  1. distillationThe formed ethanol was distilled off
  2. temperatureThe whole was cooled
  3. customthe solid product was crystallized from a mixture of ethanol and acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-a0dfdaf499cb4eccbaabccd7821fded5
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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