HCID 178507510, compound → HCID 178522487, compound

HRID 1844976Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:16]2[NH:17][C:18]([NH:20][C:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][N:24]=3)=[O:22])=[N:19][C:15]=2[CH:14]=[CH:13][CH:12]=1)=O>CC(O)=O>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:11]1[C:16]2[NH:17][C:18]([NH:20][C:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][N:24]=3)=[O:22])=[N:19][C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 169 mg (0.4 mmol) of isoquinoline-1-carboxylic acid [7-(2-amino-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-amide in AcOH (15 mL) was added NH4OAc (0.5 g). The mixture was heated at 130° C. for 30 min. After cooling to room temperature, the AcOH was removed under reduced pressure, extracted with EtOAc (50 mL), washed with sat. aq. sodium bicarbonate solution and brine. The organic phase was dried over sodium sulfate and concentrated. The residue was dissolved in DCM (3 mL), and 5 mL of hexane was added. The resulting solid was filtered and dried to afford 120 mg (75%) of isoquinoline-1-carboxylic acid (1H,3′H-[2,4′]bibenzoimidazolyl-2′-yl)-amide. LCMS: 405 (M+1)+.

Workup

temperatureAfter cooling to room temperature
customthe AcOH was removed under reduced pressure
extractionextracted with EtOAc (50 mL)
washwashed with sat. aq. sodium bicarbonate solution and brine
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated
dissolutionThe residue was dissolved in DCM (3 mL)
addition5 mL of hexane was added
filtrationThe resulting solid was filtered
customdried

Sources & evidence

ORD record: ord-4037f57d27f04617bc298452fa2c0c2c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946259B2

Reaction notes

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