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

HRID 81942Notes

Reaction equation

HRID 81942 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 148 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-a51574569d4e4417a8350e0dd4bd9ab2
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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