Dimethylformamide → HCID 18506854, compound

HRID 1355457Notes

Reaction equation

HRID 1355457 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:24].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[Cl:24][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 185069372-(6-Hydroxymethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Product 1

HCID 18506854HCID 18506854, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-(6-Hydroxymethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (0.300 g, 0.29 mmol) was stirred in 5 mL anh DCM under N2. Anhydrous DMF (0.100 mL, 1.29 mmol) and POCl3 (0.120 mL, 1.29 mmol) were added. After 15 h the reaction was diluted with water and the pH was adjusted to 9 with sat NaHCO3 (aq). The dCM was removed in vacuo and the precipitate which formed was filtered and washed with water to provide the titled compound. 1H NMR (DMSO-d6) δ12.35 (s, 1H), 8.29 (s, 1H), 7.85 (t, 1H, J=7.8 Hz, 7.21 (d, 1H, 7.3 Hz), 7.11 (d, 1H, 8.2 Hz), 4.85 (s, 2H).

Workup

  1. customThe dCM was removed in vacuo
  2. customthe precipitate which formed
  3. filtrationwas filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-d9dceb4969fd448a8f3338d47d4e178e
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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