Dimethylformamide → HCID 131724229, compound

HRID 431295Notes

Reaction equation

HRID 431295 reaction equation
CC[N:3]([CH:7](C)C)C(C)C.[ClH:10].[NH2:11][CH2:12][CH:13]([C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])=[C:17]([CH3:33])[CH:16]=1)[OH:14].C[N:35](C=O)C>CCOCC>[ClH:10].[CH3:21][C:19]1[CH:20]=[C:15]([CH:13]([OH:14])[CH2:12][NH+:11]=[C:7]([NH2:3])[NH2:35])[CH:16]=[C:17]([CH3:33])[C:18]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 70039570HCID 70039570, compound

Product 1

HCID 131724229HCID 131724229, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1H-1-Carboxamidine hydrochloride (271 mg,1.85 mmol), and DIPEA (0.5 mL, 3.87 mmol) were added to a vigorously stirring solution of amine 13 (450 mg, 1.42 mmol) in DMF (1.5 ml). The reaction was stirred for 14 hrs then worked up by diluting with Et2O. The viscous oil was repeatedly washed with Et2O, then recrystillized from CH2Cl/MeOH2 giving pure 14 (382 mg, 68%) as a off-white solid: 1H NMR (270 MHz, DMSO-d6) δ8.16(d, J=8.2 Hz, 1H, ArNO2) 8.03(d, J=8.2 Hz ArNO2), 1H, 7.87(t, J=8.2 Hz, 1H ArNO2), 7.66(t, J=8.2 Hz, 1H, ArNO2), 7.45(t, J=5.2 Hz, 1H, RCH2NH), 7.11(s, 2H, Ar—H), 5.80(d, J=4.1 Hz, LH RO—H), 5.14(s, 2H, ArOCH2Ar(NO2)), 4.60 (m, 1H, ArCH(OH)), 3.31 (m, 2H, CH2NH), 2.21(s, 6H, ArCH3) 13C NMR (67.5 MHz, MeOH-d4)δ159.3, 156.3, 148.2, 138.7, 135.1, 135.1, 132.1, 129.9, 129.6, 127.7, 125.8, 73.0, 71.3, 50.0, 16.8;

Workup

  1. washThe viscous oil was repeatedly washed with Et2O

Sources & evidence

ORD record
ord-c1af4c5e7805469cb18bb5dee525a50d
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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