Sodium hydride → 2-(7-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)-N-methylacetamide

HRID 1522643Notes

Reaction equation

[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]4[CH:22]=[N:23][NH:24][C:17]=34)[CH:12]=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:28][C:29]([NH:31][CH3:32])=[O:30]>CN(C=O)C>[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[C:17]4[C:18](=[CH:22][N:23]([CH2:28][C:29]([NH:31][CH3:32])=[O:30])[N:24]=4)[N:19]=[CH:20][CH:21]=3)[CH:12]=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(3′-Fluoro-6′-methyl-2,2′-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (50 mg, 0.156 mmol) and NaH (3.75 mg, 60% in oil, 0.15 mmol) were combined in DMF (2 mL). 2-Bromo-N-methylacetamide (23.72 mg, 0.15 mmol) was added and the mixture heated in a microwave at 80° C. for 15 minutes and then at 100° C. for 30 minutes and finally at 110° C. for a further 45 minutes. The reaction mixture was cooled and purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-25% acetonitrile (containing 10 mM NH4HCO3) in water (containing 10 mM NH4HCO3) to give the title compound. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.60 (s, 3H) 2.81 (s, 3H) 5.11 (s, 2H) 7.08 (br. s., 1H) 7.41 (d, J=8 Hz, 1H) 7.50 (br. s., 1H) 7.65 (t, J=12 Hz, 1H) 7.92 (br. s., 1H) 8.08 (d, J=8 Hz, 1H) 8.28 (br. s., 1H) 8.68 (br. s., 1H) MS [M+H] found 392.1.

Workup

waitfinally at 110° C. for a further 45 minutes
temperatureThe reaction mixture was cooled
custompurified by preparative HPLC
washeluting with a gradient of 20-25% acetonitrile (containing 10 mM NH4HCO3) in water (containing 10 mM NH4HCO3)

Sources & evidence

ORD record: ord-8016628221f540c78cab83a2f106f7ad
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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