Ammonium formate → HCID 69304361, compound

HRID 1972978Notes

Reaction equation

HRID 1972978 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([C:24]#[N:25])=[C:10]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1.C([O-])=O.[NH4+]>CO.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([C:24]#[N:25])=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69303364HCID 69303364, compound

Product 1

HCID 69304361HCID 69304361, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 4-(4-amino-6-cyanopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate (160 mg, 0.47 mmol) in MeOH (32 mL) and EtOAc (16 mL), was added Pd(OH)2 (164 mg, 0.118 mmol) followed by ammonium formate (592 mg, 9.40 mmol). The mixture was heated at 65° C. for 1.5 h then cooled to rt. The mixture was filtered through Celite® and the cake was washed with EtOAc (10 mL) and MeOH (10 mL). The filtrate was concentrated to dryness. ISCO® purification (50% EtOAc/Hexane) afforded pure product (56.6 mg, 35%). 1H NMR (400 MHz, DMSO-d6 δ 8.08 (s, 2H), 7.98 (s, 1H), 7.23 (s, 1H), 4.12-4.04 (m, 4H), 3.59-3.50 (m, 1H), 1.98-1.78 (m, 4H), 1.41 (s, 9H); LC-MS m/z[M+H]+ 343.1, RT 3.05 min.

Workup

  1. temperaturethen cooled to rt
  2. filtrationThe mixture was filtered through Celite®
  3. washthe cake was washed with EtOAc (10 mL) and MeOH (10 mL)
  4. concentrationThe filtrate was concentrated to dryness
  5. customISCO® purification (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-0522b912e9b849048772ea75b612454f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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