Water → HCID 53327269, compound

HRID 1259342Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19]CC)=O)=[C:13]([CH2:22]Br)[N:12]=2)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].[NH2:24][C:25]1[CH:26]=[N:27][N:28]([CH2:30][C:31]#[N:32])[CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[C:13]3[CH2:22][N:24]([C:25]4[CH:26]=[N:27][N:28]([CH2:30][C:31]#[N:32])[CH:29]=4)[C:17](=[O:19])[C:14]3=[CH:15][CH:16]=2)[CH:6]=[N:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

As shown in step 8-iv of Scheme 8, a solution of the above mixture (Compound 2029, 2.2 g, about 60% pure) in DMF (40 mL) at 0° C. was added dropwise over 2 hours to a suspension of 2-(4-amino-1H-pyrazol-1-yl)acetonitrile (844 mg, 6.9 mmol) and sodium carbonate (732 mg, 6.9 mmol) in DMF (20 mL). After addition was complete, the reaction mixture was stirred at 0° C. for 2 hours and heated at 80° C. for 15 hours. Additional sodium carbonate (732 mg) was added and the reaction mixture was heated at 90° C. for an additional 7 hours. After cooling, the mixture was poured into water and a precipitate formed. The solid was collected by filtration, washed with methyl t-butyl ether, and dried under high vacuum to provide 2-(4-(2-(5,6-dimethoxypyridin-3-yl)-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-1H-pyrazol-1-yl)acetonitrile (Compound 25, 450 mg).

Workup

additionAfter addition
temperatureheated at 80° C. for 15 hours
temperaturethe reaction mixture was heated at 90° C. for an additional 7 hours
temperatureAfter cooling
customa precipitate formed
filtrationThe solid was collected by filtration
washwashed with methyl t-butyl ether
customdried under high vacuum

Sources & evidence

ORD record: ord-c7f4b0f5c9694538adac27d029892cf6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466288B2

Reaction notes

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