Water → HCID 178512747, compound

HRID 492092Notes

Reaction equation

HRID 492092 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2.Cl.[N:24]1([C:29](N)=[NH:30])C=CC=N1.C(N(CC)C(C)C)C.O>CN(C=O)C>[NH:1]([CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2)[C:29]([NH2:30])=[NH:24]

Participants

6

Reactant 4

HCID 962WaterHCID 521913N,N-Diethyl-2-propanamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 57678964N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

Product 1

HCID 178512747HCID 178512747, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide, 1H-pyrazol-1-carboxamidine hydrochloride and diethyl isopropylamine are dissolved in DMF, and the reaction mixture is heated to 100° C., then cooled and diluted by addition of of water. The aqueous mixture is extracted with EtOAc, and the combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure to give N-(5-Guanidinomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide. 5-Guanidinomethyl-5,6,7,8-tetrahydro-naphthalene-2-sulfonic acid phenylamide may be similarly prepared.

Workup

  1. temperaturecooled
  2. extractionThe aqueous mixture is extracted with EtOAc
  3. dry with materialthe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d612157112d348e8bccc63f47f406d12
Source dataset
uspto-grants-2009_05
Patent number
US07531577B2

Reaction notes

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