Acetic Acid → HCID 86663055, compound

HRID 2410828Notes

Reaction equation

HRID 2410828 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:18]=[C:17]([Br:19])[CH:16]=C(C(N)=O)[C:11]=3[NH:12][C:13]=2[CH:14]=1.C=O.[C:25]([OH:28])(=O)[CH3:26].[NH3:29].[CH3:30]O>C1COCC1.O.C(#N)C>[Br:19][C:17]1[CH:16]=[C:26]([C:25]([NH2:29])=[O:28])[C:11]2[NH:12][C:13]3[CH:14]=[C:6]([N:2]([CH3:1])[CH3:30])[CH:7]=[CH:8][C:9]=3[C:10]=2[N:18]=1

Participants

10

Reactant 6

HCID 176Acetic AcidHCID 222AmmoniaHCID 712FormaldehydeHCID 887Methanol3×HCID 5003444Sodium cyanoborohydrideHCID 86663054HCID 86663054, compound

Product 1

HCID 86663055HCID 86663055, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanoborohydride (0.655 mL, 0.655 mmol, 1.0 M in THF) was added to a mixture of 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxamide (100 mg, 0.262 mmol), formaldehyde (0.21 mL, 2.6 mmol, 37% aq. solution), and acetic acid (0.45 mL, 0.79 mmol), in a mixture of MeOH (1 mL) and THF (1 mL). After stirring for 1 hr, this was diluted with MeOH and preparative HPLC (PHENOMENEX® Luna C18 30×100 10u Column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile, 30 to 100% B over 20 min at 30 mL/min) followed by SCX capture and release with 2 N solution NH3 in MeOH afforded 2-bromo-7-(dimethylamino)-5H-pyrido[3,2-b]indole-4-carboxamide (70 mg, 0.17 mmol, 66% yield) as a yellow solid. MS (ESI) m/z 333.02 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.24 (1H, s), 8.37 (1H, br. s.), 7.91 (1H, d, J=8.85 Hz), 7.82 (2H, s), 6.95 (1H, s), 6.80 (1H, dd, J=8.85, 2.14 Hz), 3.04 (6H, s).

Sources & evidence

ORD record
ord-f7ddd58747cd41cbabebdd468067faee
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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