Triethylamine → 2-Nitrobenzamide

HRID 619278Notes

Reaction equation

HRID 619278 reaction equation
C(OC(NC(=NC(OCC1C=CC=CC=1)=O)SC)=O)C1C=CC=CC=1.O.Br.Br.N1C2=NC=CC([NH:38][C:39](=[O:52])[C:40]3[CH:45]=[CH:44][C:43]([C@H](N)C)=[CH:42][C:41]=3[N+:49]([O-:51])=[O:50])=C2C=N1.C(N(CC)CC)C>CO>[N+:49]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[C:39]([NH2:38])=[O:52])([O-:51])=[O:50]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 69823849(R)-N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-(1-aminoethyl)-2-nitrobenzamide dihydrobromide monohydrate

Product 1

HCID 118762-Nitrobenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

N,N'-dibenzyloxycarbonyl-S-methylisothiourea (215 mg) was added to a mixture of (R)-N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-(1-aminoethyl)-2-nitrobenzamide dihydrobromide monohydrate (224 mg), triethylamine (0.25 ml) and methanol (5 ml) at room temperature, and the mixture was stirred at room temperature for 14 hours and at 40° C. for 7.5 hours. After the reaction, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 166 mg of (R)-N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-(1-(2',3'-dibenzyloxycarbonyl)guanidinoethyl))-2-nitrobenzamide as a pale-yellow oil.

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a77e88c03525466aa391afa0be95666e
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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