Sodium hydride → HCID 59577440, compound

HRID 1947547Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:13].Cl.Cl[CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([O:26][C:27]3[S:28][C:29]4[C:30]([N:35]=3)=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][C:20]=2[O:19][CH:18]=1>CN(C=O)C>[S:28]1[C:29]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[N:35]=[C:27]1[O:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][N:3]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:6][CH2:5][C:4]3=[O:13])=[CH:18][O:19][C:20]=2[CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 60% NaH (68 mg, 1.7 mmol) in DMF (2.5 mL) at 0° C. was added a solution of 3,4-dihydro-1H-quinolin-2-one (208 mg, 1.4 mmol) in DMF (2.0 mL). The reaction mixture was stirred (0° C., 30 min) before the addition of 2-(3-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine hydrochloride (50 mg, 0.14 mmol). The reaction mixture was stirred (rt, 30 min), washed with water, extracted with ethyl acetate, dried, filtered and concentrated. The residue was purified by reverse phase HPLC to provide the title compound (22 mg, 36%). MS (ESI): mass calcd. for C24H17N3O3S, 427.10; m/z found, 428.0 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.54-8.48 (m, 1H), 8.43-8.36 (m, 1H), 7.88-7.81 (m, 1H), 7.78 (d, J=8.5, 1H), 7.64 (d, J=2.1, 1H), 7.44-7.38 (m, 2H), 7.36-7.30 (m, 1H), 7.30-7.16 (m, 2H), 7.05-6.98 (m, 1H), 5.38 (s, 2H), 2.98-2.85 (m, 2H), 2.79-2.70 (m, 2H).

Workup

stirringThe reaction mixture was stirred (rt, 30 min)
washwashed with water
extractionextracted with ethyl acetate
customdried
filtrationfiltered
concentrationconcentrated
customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-688e49b726244dc5bc718fc7f259e466
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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