1,3-Propanediamine → HCID 13687221, compound

HRID 365221Notes

Reaction equation

HRID 365221 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:35][CH2:36][NH:37][CH2:38][CH2:39][OH:40])[N:7]=[C:8]3[C:17]4[C:12](=[C:13]([O:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:14]=[CH:15][C:16]=4[O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:11](=[O:34])[C:10]=1[C:9]=23.[CH2:41]([NH2:45])[CH2:42][CH2:43][NH2:44].CO.ClCCl>C(N(CC)CC)C>[NH2:44][CH2:43][CH2:42][CH2:41][NH:45][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:35][CH2:36][NH:37][CH2:38][CH2:39][OH:40])[N:7]=[C:8]3[C:17]4[C:12](=[C:13]([O:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:14]=[CH:15][C:16]=4[O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:11](=[O:34])[C:10]=1[C:9]=23

Participants

6

Reactant 4

HCID 4281,3-PropanediamineHCID 887MethanolHCID 6344DichloromethaneHCID 135584525-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd]-pyrazol-6(2H)-one

Product 1

HCID 13687221HCID 13687221, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
130 °C

Procedure

Under a slow stream of argon gas, a mixture of 19.4 g (0.035 mol) of crude 5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd]-pyrazol-6(2H)-one (2) and 29 ml (25.8 g, 0.35 mol) of 1,3-propanediamine was stirred at 130° C. for 3.5 hours, allowed to cool and triturated with water and 2-propanol. The solid was collected, washed successively with water, 2-propanol and ethanol, and dried under vacuum at 40° C. to give 16.9 g of crude product. Chromatography over 1 kg of silica gel (230-400 mesh) with a mixture of methanol:dichloromethane:triethylamine in the following ratios: 20:79:1, then 30:69:1, and finally 40:59:1 provided 11 g. This material was recrystallized from pyridine, washed with 2-propanol, and dried under vacuum overnight at 60° C. to afford 9.7 g (46.8%) of 3, mp 204°-206° C.

Workup

  1. temperatureto cool
  2. customtriturated with water and 2-propanol
  3. customThe solid was collected
  4. washwashed successively with water, 2-propanol and ethanol
  5. customdried under vacuum at 40° C.
  6. customto give 16.9 g of crude product
  7. customThis material was recrystallized from pyridine
  8. washwashed with 2-propanol
  9. customdried under vacuum overnight at 60° C.

Sources & evidence

ORD record
ord-411ef27f308f43e9b3e9f4fef6d13379
Source dataset
uspto-grants-1986_08
Patent number
US04608439

Reaction notes

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