Potassium Carbonate → N-(4-amino-6-chloro-9H-beta-carbolin-8-yl)-nicotinamide

HRID 552218Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=3)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([NH:24]C(=O)C(F)(F)F)[C:5]2=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:24][C:6]1[C:5]2[C:4]3[C:12](=[C:13]([NH:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=4)[CH:14]=[C:2]([Cl:1])[CH:3]=3)[NH:11][C:10]=2[CH:9]=[N:8][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-β-carbolin-8-yl]-nicotinamide (38 mg, 0.088 mmol, 1 equiv.) was suspended in 5 ml of MeOH and a 2 ml aqueous solution of K2CO3 (121 mg, 0.92 mmol, 10 equiv.) was added thereto. The resulting clear solution was heated at 60° C. for 11 hr. After cooling to RT, fine solids precipitated that were captured by filtration and washed with 10 ml of water to give 2.78 mg (10%) of N-(4-amino-6-chloro-9H-β-carbolin-8-yl)-nicotinamide. 1H-NMR (300 MHz, DMSO-d6): δ 11.32 (s, 1H), 10.56 (s, 1H), 9.26 (s, 1H), 8.82 (d, 1), 8.42 (d, 1), 8.36 (s, 1H), 8.18 (s, 1H), 7.79 (s, 1H), 7.70 (s, 1H), 7.64 (m, 1H), 5.91 (br, 2H). Formic acid standard conditions. DAD RT=1.55 min. M+H=338.

Workup

temperatureAfter cooling to RT
customfine solids precipitated
filtrationthat were captured by filtration
washwashed with 10 ml of water

Sources & evidence

ORD record: ord-c6b75418f07546ffa7a92b89730cacc1
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951801B2

Reaction notes

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