Water → N-(4-amino-6-chloro-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

HRID 552217Notes

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:31]([O-])([O-])=O.[K+].[K+].O>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][C:18]=4[CH3:31])[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 (41 mg, 0.092 mmol, 1 equiv.) was suspended in 5 ml of MeOH and a 2 ml aqueous solution of K2CO3 (127 mg, 0.92 mmol, 10 equiv.) was added thereto. The resulting clear solution was heated at 60° C. for 16 hr and then allowed to cool to RT. Additional water was added producing fine solids that were captured by filtration, washed once with 10 ml of 5% MeOH in Et2O, and dried under high vacuum to give 18 mg of N-(4-amino-6-chloro-9H-β-carbolin-8-yl)-2-methyl-nicotinamide as powdery yellow solids (56% yield). 1H-NMR (300 MHz, DMSO-d6): δ 11.18 (s, 1H), 10.41 (s, 1H), 8.62 (d, J=3.6, 1H),), 8.32 (s, 1H), 8.20 (s, 1H), 8.11 (d, J=7.5, 1H), 7.91 (s, 1H), 7.79 (s, 1H), 7.43 (m, 1H), 5.91 (br, 2H), 2.66 (s, 3H). Formic acid standard conditions. DAD RT=1.63 min. M+H=352.

Workup

temperatureto cool to RT
customproducing fine solids that
filtrationwere captured by filtration
washwashed once with 10 ml of 5% MeOH in Et2O
customdried under high vacuum

Sources & evidence

ORD record: ord-387ec3107e29402cb8fbd66a2cfe7265
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951801B2

Reaction notes

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