Hydrochloric Acid → 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine

HRID 2283751Notes

Reaction equation

HRID 2283751 reaction equation
C(OC([NH:8]C1C(B(O)O)=CC=CN=1)=O)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+].[CH3:25][CH:26]([CH3:45])[CH2:27][C:28]1[N:29]([CH2:42][CH2:43][CH3:44])[N:30]=[C:31]2[C:40]=1[C:39]1[CH:38]=[CH:37][CH:36]=C[C:34]=1[N:33]=[C:32]2[NH2:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][CH:26]([CH3:45])[CH2:27][C:28]1[N:29]([CH2:42][CH2:43][CH3:44])[N:30]=[C:31]2[C:40]=1[C:39]1[CH:38]=[CH:37][CH:36]=[N:8][C:34]=1[N:33]=[C:32]2[NH2:41]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 112775352H-Pyrazolo[3,4-c]quinolin-4-amine, 1-(2-methylpropyl)-2-propyl-HCID 22135186(2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid

Product 1

HCID 577175911-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amineYield 11.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent2×HCID 1140TolueneSolvent

Procedure

A modification of the method described in Example 16 was used to treat 2-tert-butoxycarbonylamino-3-pyridylboronic acid (11.33 mmol) in 1-propanol (10 mL) with hydrochloric acid (12 mL of 1 M) followed by sodium carbonate (1.99 g, 18.8 mmol), 4-bromo-5-(2-methylpropyl)-1-propyl-1H-pyrazole-3-carbonitrile (1.53 g, 5.66 mmol, prepared as described in Example 1) in 1-propanol (5 mL), triphenylphosphine (44.5 mg, 0.17 mmol), and palladium (II) acetate (13 mg, 0.057 mmol) in toluene (0.25 mL). The reaction was complete after it was heated overnight. Following the work-up procedure and purification, 0.18 g of 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine was obtained as off-white needles, mp 257-260° C.

Workup

  1. temperaturewas heated overnight
  2. customthe work-up procedure and purification

Sources & evidence

ORD record
ord-afb5c58d599c4e6385e58a17605afa57
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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