Ammonium Hydroxide → HCID 21929458, compound

HRID 1243830Notes

Reaction equation

HRID 1243830 reaction equation
O.O[N:3]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:24]1([C:30]2([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:38][C:37]3[NH:36][N:35]=[C:34]([C:39](O)=[O:40])[C:33]=3[CH:32]=[CH:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[NH4+]>C(Cl)(Cl)Cl>[C:24]1([C:30]2([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:38][C:37]3[NH:36][N:35]=[C:34]([C:39]([NH2:3])=[O:40])[C:33]=3[CH:32]=[CH:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 219286736,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxylic acid

Product 1

HCID 21929458HCID 21929458, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

0.718 g of 1-hydroxybenzotriazole hydrate and 1.27 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added to 1.4 g of 6,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxylic acid in suspension in 200 cm3 of chloroform. After stirring for 30 minutes at a temperature in the region of 20° C., 1.5 cm3 of aqueous 28% ammonium hydroxide solution are added dropwise to the reaction mixture. After stirring at a temperature in the region of 20° C. for about 20 hours, the reaction mixture is diluted with 300 cm3 of chloroform and washed with three times 100 cm3 of water. The organic phases are dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). The solid is taken up in 10 cm3 of dichloromethane, cooled to a temperature in the region of 5° C., drained by suction, washed with three times 5 cm3 of diisopropyl ether and dried over potassium hydroxide under reduced pressure (13 kPa), at a temperature in the region of 20° C. 1.2 g of 6,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxamide are thus obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Workup

  1. additionare added dropwise to the reaction mixture
  2. washwashed with three times 100 cm3 of water
  3. dry with materialThe organic phases are dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  6. temperaturecooled to a temperature in the region of 5° C.
  7. washwashed with three times 5 cm3 of diisopropyl ether
  8. dry with materialdried over potassium hydroxide under reduced pressure (13 kPa), at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-13562320743a47ada3747c9da8a63ba9
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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