Methanol → HCID 68564900, compound

HRID 640806Notes

Reaction equation

HRID 640806 reaction equation
C([O:4][C:5]1[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[N:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)(C)C.B(Cl)(Cl)[Cl:22].CO>ClCCl>[ClH:22].[N:15]1([C:6]2[C:5]([OH:4])=[C:14]3[C:9]([CH:10]=[CH:11][CH:12]=[N:13]3)=[CH:8][N:7]=2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 59256613HCID 59256613, compound

Product 1

HCID 68564900HCID 68564900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 8-isopropoxy-7-morpholin-4-yl-[1,6]naphthyridine (149 mg, 0.545 mmol) in dichloromethane (10 mL) at 0° C. was added BCl3 (1.5 mL of a 1 M solution in dichloromethane). The dark orange solution was left to stir at room temperature for 24 h. MeOH (10 mL) was added and the mixture concentrated. This process was repeated four times. Further washing of the remaining residue with diethyl ether (5 mL×2) provided 7-morpholin-4-yl-[1,6]naphthyridin-8-ol hydrochloride as a dark red solid (quantitative yield).—1H NMR (CD3OD): δ 9.09 (dd, J=1.5 and 5.1, 1H), 9.02 (s, 1H), 8.99 (dd, J=1.5 and 8.2, 1H), 7.79 (dd, J=5.1 and 8.2, 1H), 3.95 (m, 4H), 3.80(m, 4H).

Workup

  1. waitThe dark orange solution was left
  2. concentrationthe mixture concentrated
  3. washFurther washing of the remaining residue with diethyl ether (5 mL×2)

Sources & evidence

ORD record
ord-750666e4d7734ca39b74434605109f98
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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