Sodium Carbonate → HCID 178479144, compound

HRID 1422445Notes

Reaction equation

HRID 1422445 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=1.[Cl:13]C(Cl)(Cl)[C:15]([C:17]1[NH:18][CH:19]=[CH:20][CH:21]=1)=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:13].[NH2:12][C:9]1[NH:10][CH:11]=[C:7]([CH2:6][CH2:5][CH2:4][NH:3][C:15]([C:17]2[NH:18][CH:19]=[CH:20][CH:21]=2)=[O:16])[N:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3214872-(Trichloroacetyl)pyrroleHCID 178478696HCID 178478696, compound

Product 1

HCID 178479144HCID 178479144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-amino-propyl)-1H-imidazol-2-ylamine dihydrochloride 16 (0.100 g, 0.458 mmol), 2-trichloroacetyl pyrrole 6 (0.103 g, 0.488 mmol), and anhydrous sodium carbonate (0.172 g, 1.63 mmol), were dissolved in anhydrous N,N-dimethylformamide (5 mL). The reaction was stirred at ambient temperature for 16 h. Evaporation of the reaction under reduced pressure and purification of the residue by column chromatography (CH2Cl2/MeOH sat. NH3 85:15) afforded the desired compound in its free base form. Addition of a single drop of concentrated hydrochloric acid to a methanol solution (8 mL) and evaporation under reduced pressure yielded 0.078 g (63%) of the title compound 17 as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.07 (s, 1H), 11.59 (s, 1H), 11.45 (s, 1H), 8.14 (t, 1H, J=5.1 Hz), 7.30 (s, 2H), 6.81 (m, 2H), 6.74 (s, 1H), 6.59 (s, 1H), 6.04 (s, 1H), 3.19 (dt, 2H, J=6.6, 12.6 Hz), 2.42 (t, 2H, J=6.9 Hz), (tt, 2H, J=6.6, 13.8 Hz); 13C NMR (100 MHz, DMSO-d6) δ 160.74, 146.76, 126.43, 126.40, 121.13, 110.28, 108.65, 108.50, 37.59, 28.14, 21.60; HRMS (ESI) calcd for C11H16N5O (MH+) 234.1349, found 234.1354.

Workup

  1. customEvaporation of the reaction
  2. customunder reduced pressure and purification of the residue by column chromatography (CH2Cl2/MeOH sat. NH3 85:15)

Sources & evidence

ORD record
ord-d718ff9c3b3f4d48a9f132746c2014d2
Source dataset
uspto-grants-2015_01
Patent number
US08927029B2

Reaction notes

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