Dimethylformamide → (4-Chloromethyl-pyridin-2-yl)-(5-phenyl-thiazol-2-yl)-amine

HRID 1355509Notes

Reaction equation

HRID 1355509 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[CH:18]=[C:17]([CH2:19]O)[CH:16]=[CH:15][N:14]=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.P(Cl)(Cl)([Cl:28])=O>C(Cl)Cl>[Cl:28][CH2:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:10]2[S:11][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][N:9]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 11150268[2-(5-Phenyl-thiazol-2-ylamino)-pyridin-4-yl]-methanol

Product 1

HCID 11335641(4-Chloromethyl-pyridin-2-yl)-(5-phenyl-thiazol-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(5-Phenyl-thiazol-2-ylamino)-pyridin-4-yl]-methanol 8-7 (0.500 g, 1.77 mmol) was stirred in anh CH2Cl2 (5 mL) under N2. N,N-Dimethylformamide (0.137 mL, 1.76 mmol, 1 equiv) was added followed by the addition of phosphorous oxychloride (0.165 mL, 1.76 mmol). After 1.5 h the reaction was concentrated and quenched by the addition of saturated NaHCO3 (aq). A precipitate formed which was filtered and washed with water to provide the titled compound. 1H NMR (DMSO-d6) δ 11.49 (bs, 1H), 8.34 (d, 1H, J=5.2 Hz), 7.81 (s, 1H), 7.60 (d, 2H, J=7.7 Hz), 7.39 (t, 2H, J=7.6 Hz), 7.26 (t, 1H, 7.0 Hz), 7.13 (s, 1H), 6.99 (d, 1H, J=5.3 Hz), 4.77 (s, 2H).

Workup

  1. concentrationAfter 1.5 h the reaction was concentrated
  2. customquenched by the addition of saturated NaHCO3 (aq)
  3. customA precipitate formed which
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-75e0f6cd3c194a508f9fceda63b8955b
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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