Hydrochloric Acid → Ethyl beta-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]3-pyridine-propanoate

HRID 726717Notes

Reaction equation

HRID 726717 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1)#[N:2].Cl.Cl.[NH2:22][CH:23]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([N:39](C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[Cl-].[NH4+].[OH-].[NH4+]>CN(C)C=O.C(O)C>[NH2:39][N:2]=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH:22][CH:23]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:14])=[CH:18][CH:19]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 197073993-[4-Cyanobenzyl]aminobenzoic acidHCID 22608516Ethyl 3-amino-3-(pyridin-3-yl)propanoate dihydrochloride

Product 1

HCID 86751963Ethyl beta-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]3-pyridine-propanoateYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

3-[4-cyanobenzyl]aminobenzoic acid (0.5 g; 2 mmoles), ethyl β-amino-β-(3-pyridyl)-propanoate dihydrochloride (0.46 g; 1.7 mmoles), diisopropylethylamine (0.52 g; 4 mmoles) and benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.88 g; 2 mmoles) were stirred in N,N-dimethylformamide (25 ml) at room temperature for 1 hr. The reaction mixture was taken down to dryness and the residue was redissolved in ethanol (30 ml). The solution was saturated with HCl gas and allowed to stir overnight. The mixture was taken down to dryness and the residue was redissolved in ethanol (20 ml). To this solution, ammonium chloride (1 g) and ammonium hydroxide (10 ml) were added. The reaction mixture was stirred at room temperature for 4 hrs. and the solvent was removed under reduced pressure. The residue was purified by HPLC using acetonitrile/water/trifluoroacetic acid system. The desired fractions were collected and lyophilized to give 530 mg of white material. FAB-MS: MH+ =446.3.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hrs
  2. customand the solvent was removed under reduced pressure
  3. customThe residue was purified by HPLC
  4. customThe desired fractions were collected

Sources & evidence

ORD record
ord-26d60085472b4fd49d05b1c8d56a5ecf
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

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