Benzoic Acid → HCID 58345029, compound

HRID 1887993Notes

Reaction equation

HRID 1887993 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[C:35]3=[N:36][CH:37]=[C:38]([C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)[CH:39]=[C:34]3[N:33]=[C:32]2[C:46]2[C:47]([NH2:52])=[N:48][CH:49]=[CH:50][CH:51]=2)=[CH:27][CH:26]=1>CC(N(C)C)=O>[NH2:52][C:47]1[C:46]([C:32]2[N:31]([C:28]3[CH:27]=[CH:26][C:25]([CH2:24][NH:23][C:1](=[O:9])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:30][CH:29]=3)[C:35]3=[N:36][CH:37]=[C:38]([C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)[CH:39]=[C:34]3[N:33]=2)=[CH:51][CH:50]=[CH:49][N:48]=1

Participants

5

Reactant 3

HCID 243Benzoic Acid2×HCID 682631,1'-Carbonyldiimidazole2×HCID 60155627HCID 60155627, compound

Product 1

HCID 58345029HCID 58345029, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

Benzoic acid (0.85 g, 7.1 mmol) and CDI (1.14 g, 7.1 mmol) were dissolved in DMA (36 ml). The reaction mixture was stirred for 1 h. 3-(3-(4-(aminomethyl)phenyl)-6-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine hydrochloride was dissolved in DMA (40 ml) and the solution of benzoic acid and CDI was added over 10 min at room temperature. The reaction was stirred for two hours at room temperature and quenched by addition of water. The product N-(4-(2-(2-aminopyridin-3-yl)-6-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)benzamide precipitated and was isolated by filtration, washed with water and ether, yielding 2.9 g (5.9 mmol, 84%) of the desired product in 98% purity. 1H NMR (DMSO-d6) 400 MHz δ: 9.15 (t, J=5.6 Hz, 1H), 9.01-9.00 (m, 1H), 8.67-8.66 (m, 1H), 8.63-8.62 (m, 1H), 8.58-8.57 (m, 1H), 8.22-8.19 (m, 1H), 8.02-8.00 (m, 1H), 7.95-7.92 (m, 2H), 7.57-7.45 (m, 8H), 7.29-7.27 (m, 1H), 7.03 (s, br, 2H), 6.45-6.42 (m, 1H), 4.59-4.58 (m, 2H) MS 498.55, [M+H].

Workup

  1. stirringThe reaction was stirred for two hours at room temperature
  2. customquenched by addition of water
  3. customThe product N-(4-(2-(2-aminopyridin-3-yl)-6-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)benzamide precipitated
  4. customwas isolated by filtration
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-e83006c2ab284bd29ecfe8c6995e4b93
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

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