Trifluoroacetic acid → 9-[(2S)-2-aminopropyl]-2-(methylamino)-9H-pyrido[2,3-b]indole-3-carboxamide

HRID 1158759Notes

Reaction equation

HRID 1158759 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH3:28])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH:19]=[C:20]([C:25]([NH2:27])=[O:26])[C:21]([NH:23][CH3:24])=[N:22][C:11]1=2)(C)(C)C.C(O)(C(F)(F)F)=O.NC1C(C(N)=O)=CC2C3C(=CC=CC=3)N(C[C@@H](N)C)C=2N=1>>[NH2:7][C@@H:8]([CH3:28])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH:19]=[C:20]([C:25]([NH2:27])=[O:26])[C:21]([NH:23][CH3:24])=[N:22][C:11]1=2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 595136442-amino-9-[(2S)-2-aminopropyl]-9H-pyrido[2,3-b]indole-3-carboxamideHCID 59513645tert-butyl{(1S)-2-[3-(aminocarbonyl)-2-(methylamino)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate

Product 1

HCID 249009299-[(2S)-2-aminopropyl]-2-(methylamino)-9H-pyrido[2,3-b]indole-3-carboxamideYield 35%

Procedure

tert-butyl{(1S)-2-[3-(aminocarbonyl)-2-(methylamino)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate xxxii-a (20 mg, 0.051 mmol) was deprotected according to the TFA procedure detailed in the preparation of 30 to afford the title compound as the trifluoroacetate salt (45, 7 mg, 35%). NH4OAc standard conditions. DAD Retention time =5.33 min. M+H=298. 1H NMR (300 MHz, CDCl3): δ 9.04 (br s, 1H), 8.76 (s, 1H), 8.02 (br s, 4H), 7.82 (d, J=7.9 Hz, 1H), 7.57 (d, J=8.5 Hz, 1H), 7.35 (br dd, J=7.3, 7.3 Hz, 1H), 7.23 (br dd, J=7.3, 7.3 Hz, 1H), 4.48-4.44 (m, 1H), 3.04 (s, 3H), 3.57-3.52 (m, 2H), 1.21 (d, J=6.1 Hz, 3H).

Sources & evidence

ORD record
ord-43593dcc425b44098d5081e5b09e6263
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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