Sodium Nitrite → HCID 68523856, compound

HRID 1437425Notes

Reaction equation

HRID 1437425 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]([NH:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH3:18])[C:13]([NH2:26])=[CH:12][CH:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[N:27]([O-])=O.[Na+]>C(O)(=O)C>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]4[N:16]([C@H:17]([C:19]5[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=5)[CH3:18])[N:27]=[N:26][C:13]4=[CH:12][CH:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 68521442(S)-N6-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine

Product 1

HCID 68523856HCID 68523856, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (S)—N6-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine (Method 9; 0.08 g, 0.2 mmol), in aqueous acetic acid (5%, 3 ml) was slowly added the aqueous NaNO2 (0.01 g, 0.2 mmol, 1 ml H2O) solution at 25° C. The reaction was allowed to stir for an additional 5 minutes, then quenched with water (10 ml), and extracted with DCM (3×25 ml). The combined organic was washed with saturated NaHCO3 (50 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM:MeOH=40:1) to give the title compound (0.037 g, 50%). NMR (400 MHz, CD3OD) 8.02 (d, J=8.9 Hz, 1H), 7.46-7.42 (m, 2H), 7.08-7.04 (m, 2H), 6.91 (d, J=8.9 Hz, 1H), 6.23-6.19 (m, 2H), 2.12 (d, J=7.0 Hz, 3H), 1.95-1.91 (m, 1H), 1.02-1.00 (m, 2H), 0.75-0.72 (m, 2H). MS: Calcd.: 363. Found: [M+H]+ 364.

Workup

  1. customquenched with water (10 ml)
  2. extractionextracted with DCM (3×25 ml)
  3. washThe combined organic was washed with saturated NaHCO3 (50 ml)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was purified by column chromatography (DCM:MeOH=40:1)

Sources & evidence

ORD record
ord-4a146a160a4c4903b67a767bc5c94a8d
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Reaction notes

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