Isobutylamine → [4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol

HRID 1798888Notes

Reaction equation

HRID 1798888 reaction equation
C([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)C.CC(C)CN.NCC(C)(O)C.B(Br)(Br)Br>ClCCl>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][OH:3])[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 25134Boron tribromideHCID 951022-Propanol, 1-amino-2-methyl-HCID 68934983HCID 68934983, compound

Product 1

HCID 11601483[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a chilled solution (ice bath) of 2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (2.0 g, 6.69 mmol, prepared according to the general methods of Example 6 using 2-methylpropan-1-amine in lieu of 1-amino-2-methylpropan-2-ol) in dichloromethane (50 mL) was added boron tribromide (20 mL, 1M solution in dichloromethane). The mixture turned light purple and was stirred at ambient temperature for 44 hours. The reaction was quenched with methanol (20 mL) and aqueous hydrochloric acid (6N, 10 mL). After stirring for 4 hours, the pH was adjusted to 10 by the addition of aqueous sodium hydroxide (50%). Dichloromethane (50 mL) was added with stirring and the layers were separated. The aqueous fraction was extracted with chloroform (2×250 mL). The combined organic fractions were concentrated to provide 1.4 g of [4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol as a white powder, mp 226-228° C.

Workup

  1. customThe reaction was quenched with methanol (20 mL) and aqueous hydrochloric acid (6N, 10 mL)
  2. stirringAfter stirring for 4 hours
  3. additionthe pH was adjusted to 10 by the addition of aqueous sodium hydroxide (50%)
  4. additionDichloromethane (50 mL) was added
  5. stirringwith stirring
  6. customthe layers were separated
  7. extractionThe aqueous fraction was extracted with chloroform (2×250 mL)
  8. concentrationThe combined organic fractions were concentrated

Sources & evidence

ORD record
ord-11f4dbb92a984ea3a9b17820d2f4bc82
Source dataset
uspto-grants-2013_01
Patent number
US08343993B2

Reaction notes

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