Ammonium Acetate → N-(6-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

HRID 552193Notes

Reaction equation

HRID 552193 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:20])[C:14]=1[O:15][CH2:16][CH:17]1[CH2:19][CH2:18]1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH3:21][C:22]1[N:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25].C([O-])(=O)C.[NH4+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:20][C:24](=[O:25])[C:23]3[CH:27]=[CH:28][CH:29]=[N:30][C:22]=3[CH3:21])[C:14]=1[O:15][CH2:16][CH:17]1[CH2:19][CH2:18]1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 6433732-Methylnicotinic acidHCID 671652126-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-ylamine

Product 1

HCID 11281226N-(6-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-yl)-2-methyl-nicotinamideYield 40%

Procedure

The desired compound was prepared according to Method A from 6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine and 2-methylnicotinic acid in a 40-60% yield. 1H-NMR (300 MHz, MeOH-d4): 60.29 (m, 2H), 0.55 (m, 2H), 1.29 (m, 1H), 2.78 (s, 3H), 3.95 (m, 2H), 7.46 (dd, 1H), 8.08 (m, 1H), 8.30 (m, 3H), 8.59 (m, 1H), 8.81 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 2.18 min. MS (M+H+): 405.

Workup

  1. custom2.18 min

Sources & evidence

ORD record
ord-de7baad9de6b4a548d603f202a99d7e9
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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