Hydrochloric Acid → 5-[4-(2-Morpholin-4-yl-ethoxy)-phenyl]-3-(3-nitro-benzyloxy)-pyridin-2-ylamine

HRID 1627526Notes

Reaction equation

[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:11][CH:10]=2)=[CH:4][N:3]=1.NC1C(O)=CC(C2C=CC=CC=2)=CN=1.[H-].[Na+].Br[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([N+:48]([O-:50])=[O:49])[CH:43]=1.Cl>CN(C=O)C>[N:18]1([CH2:17][CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([C:5]3[CH:6]=[C:7]([O:8][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([N+:48]([O-:50])=[O:49])[CH:43]=4)[C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:10][CH:11]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-amino-5-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-pyridin-3-ol (prepared according to the procedures for 2-amino-5-phenyl-pyridin-3-ol in Example I-88 of U.S. patent application Ser. No. 10/786,610 (PCT/US2004/005495) (45.5 mg, 0.14 mmol) in DMF (3 mL) at 0° C. was added NaH (60% in oil) (5.6 mg, 0.14 mmol) and the mixture was stirred at 0° C. for 20 min. Then 1-bromomethyl-3-nitro-benzene was added and the mixture was stirred at 0° C. for 1 hr and at room temperature for 2 hr. Cold 1 N aqueous HCl (0.1 mL) was added and the solvent was removed under reduced pressure. The residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=100:3:0.3) to give 5-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-(3-nitro-benzyloxy)-pyridin-2-ylamine as yellow solid (44 mg, 68%).

Workup

stirringthe mixture was stirred at 0° C. for 1 hr and at room temperature for 2 hr
customthe solvent was removed under reduced pressure
customThe residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=100:3:0.3)

Sources & evidence

ORD record: ord-7c35323e053448e6aef8539074d0452b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785632B2

Reaction notes

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