Isopropyl isocyanate → N-(4-chloro-3-(6-(3-isopropylureido)-1H-imidazo[4,5-b]pyridin-2-yl)phenyl)furan-2-carboxamide

HRID 713692Notes

Reaction equation

HRID 713692 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)=[O:20])[CH:14]=[CH:15][C:16]=3[Cl:17])=[N:8][C:5]2=[N:6][CH:7]=1.[N:26]([CH:29]([CH3:31])[CH3:30])=[C:27]=[O:28]>CN(C=O)C>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([NH:18][C:19]([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[O:20])=[CH:12][C:11]=1[C:9]1[NH:10][C:4]2[C:5]([N:8]=1)=[N:6][CH:7]=[C:2]([NH:1][C:27]([NH:26][CH:29]([CH3:31])[CH3:30])=[O:28])[CH:3]=2

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 78425811N-(3-(6-amino-1H-imidazo[4,5-b]pyridin-2-yl)-4-chlorophenyl)furan-2-carboxamide

Product 1

HCID 85471060N-(4-chloro-3-(6-(3-isopropylureido)-1H-imidazo[4,5-b]pyridin-2-yl)phenyl)furan-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 20 mL vial was transferred N-(3-(6-amino-1H-imidazo[4,5-b]pyridin-2-yl)-4-chlorophenyl)furan-2-carboxamide I-1 (15 mg, 0.042 mmols) in DMF (2 mL), and the 2-isocyanatopropane (7 mg, 0.0.084 mmols, 2 eq) was added. The yellow reaction mixture was stirred at room temperature for 12 hrs. Checked via LCMS for the desired peak and found M+H (439). The reaction mixture was purified via preparative HPLC to isolate desired product (Compound 24). Yielded 7.2 mg, 0.016 mmols, 39%) of the desired compound.

Workup

  1. customThe reaction mixture was purified via preparative HPLC

Sources & evidence

ORD record
ord-d8de688337ff489a910a8af0bd79ae3a
Source dataset
uspto-grants-2015_11
Patent number
US09186361B2

Reaction notes

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