9-ethyl-2-(methylamino)-9H-pyrido[2,3-b]indole-3-carboxamide → tert-butyl{(1S)-2-[3-(aminocarbonyl)-2-(methylamino)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate

HRID 1158758Notes

Reaction equation

HRID 1158758 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[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:24]([NH2:26])=[O:25])[C:21]([NH2:23])=[N:22][C:11]1=2)([CH3:4])([CH3:3])[CH3:2].[CH2:29](N1C2C(=CC=CC=2)C2C=C(C(N)=O)C(NC)=NC1=2)C>>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[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:24]([NH2:26])=[O:25])[C:21]([NH:23][CH3:29])=[N:22][C:11]1=2)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 249009329-ethyl-2-(methylamino)-9H-pyrido[2,3-b]indole-3-carboxamideHCID 59513639tert-butyl {(1S)-2-[2-amino-3-(aminocarbonyl)-9h-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate

Product 1

HCID 59513645tert-butyl{(1S)-2-[3-(aminocarbonyl)-2-(methylamino)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamateYield 89%

Procedure

tert-butyl{(1S)-2-[2-amino-3-(aminocarbonyl)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate (xvi-b, 20 mg, 0.052 mmol) was alkylated according to procedure detailed in the preparation of 48, to afford tert-butyl{(1S)-2-[3-(aminocarbonyl)-2-(methylamino)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate (xxxii-a, 20 mg, 89%). NH4OAc QC conditions. M+H=398.

Sources & evidence

ORD record
ord-02f9b21527d4454f9db4f3dcf002d877
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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