Water → (S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 388133Notes

Reaction equation

C1([C@@H:7]([NH:9]C2C=C(C3C=CC=C4C=3C=CC=N4)N=CC=2N)C)C=CC=CC=1.[C:27]1([C@@H:33]([N:35]2[C:43]3[CH:42]=[C:41]([C:44]4[CH:53]=[CH:52][CH:51]=[C:50]5[C:45]=4[CH:46]=[CH:47][CH:48]=[N:49]5)N=C[C:38]=3[NH:37][C:36]2=[O:54])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.NC(N)=O.O>CN1CCCC1=O>[C:27]1([C@@H:33]([N:35]2[C:43]3[C:38](=[N:9][CH:7]=[C:41]([C:44]4[CH:53]=[CH:52][CH:51]=[C:50]5[C:45]=4[CH:46]=[CH:47][CH:48]=[N:49]5)[CH:42]=3)[NH:37][C:36]2=[O:54])[CH3:34])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 185 °C

Procedure

(S)-1-(1-Phenylethyl)-6-(quinolin-5-yl)-1H-imidazo[4,5-c]pyridin-2(3H)-one ((1S)-1-Phenylethyl)(3-amino-6-(5-quinolyl)(4-pyridyl))amine (450mg, 1.32 mmol) and urea (158 mg, 2.64 mmol) were combined in 1-methylpyrrolidin-2-one (4 mL) and heated at 185° C. for 2 h. Water (10 mL) was added and the crude product was collected by filtration. The product was purified by reverse-phase preparative HPLC (20-95% acetonitrle in water, over 30 min) to give the product (92.9 mg, 19%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.45 (s, 1H), 8.91 (dd, J=4.10, 1.76, 1H), 8.39 (d, J=0.78, 1H), 8.33 (ddd, J=8.00, 1.27, 1.07, 1H), 8.05 (d, J=8.40, 1H), 7.80 (dd, J=8.49, 7.13, 1H), 7.59 (dd, J=7.13, 1.27, 1H), 7.41-7.47 (m, 3H), 7.29-7.41 (m, 3H), H), 5.75 (d, J=7.22, 1H), 4.16 (d, J=0.78, 1H), 1.87 (d, J=7.22, 3 H); MS (ESI) m/z 367.0 [M+1]+.

Workup

filtrationthe crude product was collected by filtration
customThe product was purified by reverse-phase preparative HPLC (20-95% acetonitrle in water, over 30 min)

Sources & evidence

ORD record: ord-2c69866178b2400a9f3b403e2abb370d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372976B2

Reaction notes

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