Dimethylamine → HCID 57898973, compound

HRID 910961Notes

Reaction equation

HRID 910961 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1[N:6]=[C:7]([NH:10][C:11]2[CH:18]=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[C:14]([CH:15]=O)=[CH:13][N:12]=2)[S:8][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:1][N:2]([CH2:15][C:14]1[C:17]([O:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[CH:18][C:11]([NH:10][C:7]2[S:8][CH:9]=[C:5]([CH3:4])[N:6]=2)=[N:12][CH:13]=1)[CH3:3]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86634725HCID 86634725, compound

Product 1

HCID 57898973HCID 57898973, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (0.374 mL, 0.747 mmol) was added to a solution of 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinaldehyde (0.090 g, 0.249 mmol) in THF (3 mL) and stirred for 10 minutes. Sodium triacetoxyborohydride (0.264 g, 1.25 mmol) was added and the reaction mixture was stirred for an additional 30 minutes. The mixture was quenched with saturated sodium bicarbonate, partitioned between ethyl acetate and water, washed with brine, dried, and concentrated. The residue was dissolved in THF (2 mL), 1M HCl in ether was added, the solution was diluted in hexanes (5 mL), triturated for 15 minutes, filtered, dried to afford 5-((dimethylamino)methyl)-N-(4-methylthiazol-2-yl)-4-(naphthalen-1-yloxy)pyridin-2-amine (0.071 g, 73.0% yield) as a white solid. 1H NMR (DMSO d6) δ 10.88 (bs, 1H), 8.58 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 7.90 (d, 1H), 7.52-7.67 (m, 4H), 6.67 (s, 1H), 6.37 (s, 1H), 4.54 (s, 2H), 2.88 (s, 6H), 2.18 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred for an additional 30 minutes
  2. customThe mixture was quenched with saturated sodium bicarbonate
  3. custompartitioned between ethyl acetate and water
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in THF (2 mL)
  8. addition1M HCl in ether was added
  9. additionthe solution was diluted in hexanes (5 mL)
  10. customtriturated for 15 minutes
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-9e50e2bb31d241e181713f0175ef5220
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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