Acetone → HCID 66605060, compound

HRID 2410822Notes

Reaction equation

HRID 2410822 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)[CH:12]=[C:11]([C:25]([NH2:27])=[O:26])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[CH3:28][C:29](=O)[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(C(F)(F)F)=O.N>C(Cl)Cl.C1COCC1.CO.O>[CH:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)[CH:12]=[C:11]([C:25]([NH2:27])=[O:26])[C:7]=3[NH:8][C:9]=2[CH:10]=1)([CH3:30])[CH3:28]

Participants

9

Reactant 5

HCID 180AcetoneHCID 222AmmoniaHCID 6422Trifluoroacetic acid2×HCID 5049666Sodium triacetoxyborohydrideHCID 66604922HCID 66604922, compound

Product 1

HCID 66605060HCID 66605060, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent4×HCID 962WaterSolvent2×HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A suspension of 7-amino-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (30 mg, 0.081 mmol), propan-2-one (0.118 mL, 1.62 mmol), and sodium triacetoxyborohydride (172 mg, 0.810 mmol) in a mixture of DCM/THF (2/1) (3 mL) was stirred at RT overnight. The mixture was diluted with MeOH and preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 7-(isopropylamino)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (20 mg, 0.045 mmol, 55% yield). MS (ESI) m/z 413.20 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.13 (1H, s), 8.58 (2H, s), 8.51 (1H, s), 8.29 (1H, s), 7.90 (1H, d J=8.56 Hz), 7.81 (1H, s), 7.68-7.77 (2H, m), 6.80 (1H, d, J=1.76 Hz), 6.60 (1H, dd, J=8.56, 2.01 Hz), 6.00 (1H, d, J=7.55 Hz), 3.53-3.68 (1H, m), 1.21 (6H, d, J=6.30 Hz).

Sources & evidence

ORD record
ord-6c49d9ac301a47b2b26255a6b40dd164
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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