Diisopropylethylamine → HCID 178479467, compound

HRID 987217Notes

Reaction equation

HRID 987217 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[N:8]([C:9](=[O:34])[CH:10]=[C:11]([C:16]([NH:18][CH2:19][C@H:20]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:21]([OH:23])=[O:22])=[O:17])[CH:12]=2)[CH:7]=1.FC(F)(F)C(O)=O.NCCCOC1C=CC2N(C(=O)C=C(C(NC[C@H](NS(C3C=CC=CC=3)(=O)=O)C(O)=O)=O)C=2)C=1.C(N(C(C)C)CC)(C)C.[ClH:85].[N:86]1([C:91](N)=[NH:92])C=CC=N1>CN(C=O)C.O>[ClH:85].[C:28]1([S:25]([NH:24][C@@H:20]([CH2:19][NH:18][C:16]([C:11]2[CH:12]=[C:13]3[N:8]([C:9](=[O:34])[CH:10]=2)[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:91]([NH2:92])=[NH:86])[CH:15]=[CH:14]3)=[O:17])[C:21]([OH:23])=[O:22])(=[O:27])=[O:26])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 56636653HCID 56636653, compoundHCID 86759197HCID 86759197, compound

Product 1

HCID 178479467HCID 178479467, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (S)-3-{[7-(3-amino-propoxy)-4-oxo-4H-quinolizine-2-carbonyl]-amino}-2-benzenesulfonylamino-propionic acid trifluoroacecic acid salt (compound XIV)(15 mg, 0.025 mmol), diisopropylethylamine (13 μl, 0.075 mmol) and 1H-pyrazole-1-carboxamidine hydrochloride (6 mg, 0.038 mmol) in DMF (0.5 ml) and water (0.5 ml) was stirred at 60° C. for 7 hours. It was then concentrated and the residue was flash chromatographed (ethanol:NH4OH:water; 8:1:1) and lyophilized in a (1:1) mixture of 0.1N HCl and water to afford 11.4 mg of pure desired product as a yellow solid which was characterized by 1HNMR (400 MHz, CD3OD) δ: 2.14-2.21 (m, 2H), 3.44-3.48 (m,2H), 3.49-3.54 (dd, J=13.5 and 9.0 Hz, 1H), 3.77-3.82 (dd, J=13.5 and 5.0 Hz, 1H), 4.23-4.28 (m, 3H), 6.94 (d, J=1.5 Hz, 1H), 7.37 (s, 1H), 7.43-7.56 (m, 4H), 7.85-7.86 (m, 2H), 7.91 (d, J=9.5 Hz, 1H), 8.7 (s, 1H).

Workup

  1. concentrationIt was then concentrated
  2. customchromatographed (ethanol:NH4OH:water; 8:1:1)
  3. additionlyophilized in a (1:1) mixture of 0.1N HCl and water

Sources & evidence

ORD record
ord-7e015111bb02426c8b598465b3704472
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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