Hydrochloric Acid → HCID 66676052, compound

HRID 421653Notes

Reaction equation

HRID 421653 reaction equation
[NH2:1][C:2]1[C:3]([C:25]([NH2:27])=[O:26])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[C:6]=2[N:24]=1.[ClH:28]>CO>[ClH:28].[NH2:1][C:2]1[C:3]([C:25]([NH2:27])=[O:26])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][CH2:15][NH2:16])[C:6]=2[N:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59513636HCID 59513636, compound

Product 1

HCID 66676052HCID 66676052, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {2-[2-amino-3-(aminocarbonyl)-9H-pyrido[2,3-b]indol-9-yl]ethyl}carbamate (xvi-a, 35.0 mg, 0.095 mmol) in MeOH (2 mL) was added conc. HCl (1 mL). The reaction was stirred at RT. After 2 h, the reaction was concentrated and lyophilized to yield 2-amino-9-(2-aminoethyl)-9H-pyrido[2,3-b]indole-3-carboxamide hydrochloride as a white solid (16, 27 mg, 93%). NH4OAc standard conditions. DAD Retention time=4.48 min. M+H=270. 1H NMR (300 MHz, D2O): 8.16 (s, 1), 7.74 (d, J=7.6 Hz, 1H), 7.73-7.42 (m, 1H), 7.36-7.28 (m, 2H), 4.32 (t, J=5.7 Hz, 2H), 3.37 (t, J=5.7 Hz, 2H).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-9328b28baff542faa753e175eeefef43
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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