Methylamine → HCID 22346269, compound

HRID 897319Notes

Reaction equation

HRID 897319 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.CN.C[CH2:27][N:28](C(C)C)C(C)C>CS(C)=O.C1COCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:10]2[C:9]([OH:23])=[C:8]3[C:3]([CH:4]=[CH:5][CH:6]=[N:7]3)=[C:2]([NH:28][CH3:27])[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 22346269HCID 22346269, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (12.0 g, 32 mmol) in DMSO (48 mL) was treated with methyl amine (48 mL of a 2M solution in THF, 96 mmol) and Hunig's base (11.1 mL, 86 mmol). The vessel was purged with argon, sealed and stirred at 135C for 3 days. The reaction was cooled, quenched with water (280 mL) and the pH adjusted to 5 by the addition of acetic acid. The reaction was stirred at room temperature for 1 hr and filtered. The solids were washed with water (100 mL) and then EtOAc (50 mL), and dried in vacuo to afford the title compound as a white solid.

Workup

  1. customThe vessel was purged with argon
  2. customsealed
  3. temperatureThe reaction was cooled
  4. customquenched with water (280 mL)
  5. additionthe pH adjusted to 5 by the addition of acetic acid
  6. stirringThe reaction was stirred at room temperature for 1 hr
  7. filtrationfiltered
  8. washThe solids were washed with water (100 mL)
  9. dry with materialEtOAc (50 mL), and dried in vacuo

Sources & evidence

ORD record
ord-ea9b1c22413d4496a1b84f3eae1dfa37
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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