Sodium Hydroxide → HCID 25261018, compound

HRID 1966209Notes

Reaction equation

HRID 1966209 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[S:16][CH:17]=[C:18]([CH2:20][O:21]C(=O)C)[N:19]=2)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[S:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=2)=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 25261017HCID 25261017, compound

Product 1

HCID 25261018HCID 25261018, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Acetic acid 2-(5-phenoxy-pyridine-2-ylamino)-thiazole-4-ylmethyl ester (0.44 mmol) is suspended in ethanol (1.5 ml) and 1 M NaOH (1.5 ml) is added. The solution is stirred at RT for 3 h. The reaction solution is diluted with water. The precipitate is filtered, washed with water and dried 16 h in vacuo at 40° C. “A10” is obtained as a beige powder in yield of 88%; mp. 130.0-131.0° C.; HPLC (method C): 1.64 min; LC-MS (method A): 1.430 min, 300.15 (M+H+); 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 11.221 (s, 1H), 8.102 (d, 1H, J=2.8 Hz), 7.515 (dd, 1H, J=8.9 Hz, J=2.8 Hz), 7.389-7.349 (m, 2H), 7.125-7.083 (m, 2H), 6.996-6.972 (s, 2H), 6.687 (s, 1H), 5.105 (t, 1H, J=5.3 Hz), 4.442 (d, 2H, J=5.3 Hz).

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with water
  3. customdried 16 h in vacuo at 40° C. “A10”
  4. customis obtained as a beige powder in yield of 88%
  5. custom1.64 min
  6. custom1.430 min, 300.15 (M+H+)

Sources & evidence

ORD record
ord-5508fc6edf2a44eaabd0248dfe71c47f
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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