Acetic Acid → HCID 178427325, compound

HRID 1056941Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[F:38])=[C:4]([C:9]2[C:10]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:11]=3[C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C(O)(=O)C.[N:43]([O-])=O.[Na+]>C(OCC)(=O)C.O>[F:38][C:32]1[CH:33]=[C:34]([F:37])[CH:35]=[CH:36][C:31]=1[O:30][C:3]1[C:2]2[N:1]=[N:43][NH:8][C:7]=2[CH:6]=[CH:5][C:4]=1[C:9]1[C:10]2[CH:19]=[CH:18][N:17]([S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)(=[O:21])=[O:22])[C:11]=2[C:12](=[O:16])[N:13]([CH3:15])[CH:14]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 4-[3,4-diamino-2-(2,4-difluorophenoxyl)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.040 g, 0.074 mmol) in acetic acid (0.1 mL, 3 mmol) was treated with water (0.37 mL, 21 mmol) followed by sodium nitrite (0.026 g, 0.37 mmol) and stirred at 20° C. for 30 min. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate (2×) and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (32 mg, 78%) as a crude brown residue that was used immediately without further purification. LCMS calculated for C27H20F2N5O4S (M+H)+: m/z=548.1. found: 548.1.

Workup

washThe organic layer was washed with saturated sodium bicarbonate (2×) and brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-17cb995d487c4b40ab1a756274369c3b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399640B2

Reaction notes

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