Pyridine → 2-(6-(4-(2-Benzyloxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid

HRID 515261Notes

Reaction equation

HRID 515261 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][C:18]3[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=3)[CH:11]=2)[CH2:6][CH2:5]1.[C:26](OC(=O)C)(=O)[CH3:27].N1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C>[CH2:34]([O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][C:18]3[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=3)[CH:11]=2)[CH2:6][CH2:5]1)[C:35]1[CH:27]=[CH:26][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 498222172-((6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxylic acid2×

Product 1

HCID 866764312-(6-(4-(2-Benzyloxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acidYield 71.7%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
50 °C

Procedure

2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid (Compound 7) (30 g, 0.082 mol), pyridine (300 mL) and DMAP (0.3 g) were mixed in a four-necked flask, and acetic anhydride was added by droplet when the temperature was controlled at 30° C. After adding, it was heated up to 50° C. and reacted overnight in thermal insulation. After reaction it was cooled down to room temperature and grew the grain overnight. After air pump filtration, the cake was rinsed by suitable amount of methylene dichloride. Then the cake was taken up and put into methylene dichloride (150 mL) and stirred for 30 min at room temperature. After air pump filtration the cake was dried to constant weight by blast at 60° C. to give light yellow to off-white solid target Compound 17 (Pg is acetyl) (24 g, yield: 71.7%).

Workup

  1. customwas controlled at 30° C
  2. additionAfter adding
  3. customreacted overnight in thermal insulation
  4. customAfter reaction it
  5. temperaturewas cooled down to room temperature
  6. customthe grain overnight
  7. filtrationAfter air pump filtration
  8. washthe cake was rinsed by suitable amount of methylene dichloride
  9. filtrationAfter air pump filtration the cake
  10. customwas dried to constant weight by blast at 60° C.

Sources & evidence

ORD record
ord-3514e12c7a2d478a93ffae7c5d97400c
Source dataset
uspto-grants-2015_08
Patent number
US09108954B2

Reaction notes

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