Hydrochloric Acid → HCID 178511338, compound

HRID 2240088Notes

Reaction equation

HRID 2240088 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=O)[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:25]([NH2:28])[CH2:26][NH2:27].[BH4-].[Na+].Cl>CO>[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH:27][CH2:26][CH2:25][NH2:28])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 178519381HCID 178519381, compound

Product 1

HCID 178511338HCID 178511338, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(Naphthalene-1-sulfonyl)-1H-indazole-5-carbaldehyde (0.3 mmol) was stirred for 24 hrs with the excess of ethylene diamine (1 mmol) in methanol. Sodium borohydride (0.6 mmol) was added and stirring continued for another 24 hrs. After completion, the volatiles were removed in vacuo, crude material diluted with cold water, acidified to pH 3.4, filtered off, washed on a filter with cold water and dried to afford the target material as a free base. The latter was converted into hydrochloride salt by dissolution in methanol, followed by treatment with the excess of 2N HCl and the evacuation of the volatiles in vacuo to afford the title compound, mp>200° C.; MS (ES+) 381[M+H]+

Workup

  1. customAfter completion, the volatiles were removed in vacuo, crude material
  2. additiondiluted with cold water
  3. filtrationfiltered off
  4. washwashed on
  5. filtrationa filter with cold water
  6. customdried
  7. customto afford the target material as a free base

Sources & evidence

ORD record
ord-fdcd12511d1d4341901bd16d877fd323
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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