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

HRID 421669Notes

Reaction equation

HRID 421669 reaction equation
[NH2:1][C:2]([C:4]1[C:27]([NH:28][CH3:29])=[N:26][C:7]2[N:8]([CH2:15][C@@H:16]([NH:18]C(=O)OC(C)(C)C)[CH3:17])[C:9]3[C:14]([C:6]=2[CH:5]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:3].C(O)(C(F)(F)F)=O.NC1C(C(N)=O)=CC2C3C(=CC=CC=3)N(C[C@@H](N)C)C=2N=1>>[NH2:18][C@@H:16]([CH3:17])[CH2:15][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:5]=[C:4]([C:2]([NH2:1])=[O:3])[C:27]([NH:28][CH3:29])=[N:26][C:7]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-f1eff99305af4a11b814cdbea5b259a6
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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