Water → HCID 53236255, compound

HRID 1966703Notes

Reaction equation

HRID 1966703 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[NH2:14][C:15]1[N:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]([NH2:32])[C:24]([NH:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:25][CH:26]=2)=[CH:17][N:16]=1.O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:28]([N:27]1[C:24]2[CH:25]=[CH:26][C:21]([C:18]3[CH:17]=[N:16][C:15]([NH2:14])=[N:20][CH:19]=3)=[CH:22][C:23]=2[N:32]=[C:8]1[C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 155324822-(1,3-Thiazol-2-yl)benzaldehydeHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 53236255HCID 53236255, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-thiazol-2-yl-benzaldehyde (100 mg, 0.53 mmol) and 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (120 mg, 0.45 mmol) in acetic acid (5 mL) is warmed to 50° C. for 12 hours and then at 80° C. for 60 hours. After this time the reaction is cooled to room temperature and pour into water and NaHCO3 (sat.). The product is extracted into EtOAc (3×) and the combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2) affords the title compound (30 mg, 16%). LCMS (ESMS): m/z 427.20 (M++1)

Workup

  1. extractionThe product is extracted into EtOAc (3×)
  2. dry with materialthe combined organics are dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-eda7585eb2874241ac7fe0914dbfc015
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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