Triethylamine → HCID 69309075, compound

HRID 2117763Notes

Reaction equation

HRID 2117763 reaction equation
C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:13][C:14]([CH3:40])([CH3:39])[CH:15](O)[CH2:16][C:17]1[N:18]([CH2:35][CH2:36][CH3:37])[C:19]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:23]=2)=[CH:20][N:21]=1.N12CCCN=C1CCCCC2>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:13][C:14]([CH3:39])([CH3:40])[CH:15]=[CH:16][C:17]1[N:18]([CH2:35][CH2:36][CH3:37])[C:19]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:23]=2)=[CH:20][N:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69310638HCID 69310638, compound

Product 1

HCID 69309075HCID 69309075, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.74 ml, 5.05 mmol), followed by methane sulphonyl chloride (0.103 ml, 1.33 mmol) was added to a stirred solution of 4-[2-(3,3-dimethyl-2-hydroxybut-1-yl)-1-(propyl)imidazol-5-yl]-2-anilinopyrimidine (Method 101; 480 mg, 1.26 mmol) in DCM (40 ml) at ambient temperature and the mixture stirred for 24 hours. The volatiles were removed by evaporation and toluene (10 ml), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.38 ml, 2.54 mmol) was added to the residue. The mixture was heated at reflux for 5 hours, allowed to cool, washed with water and extracted with EtOAc. The extracts were combined, dried and the solvent removed by evaporation to give the title compound (240 mg, 53%). NMR: 0.64 (t, 3H), 1.15 (s, 9H), 1.53 (q, 2H), 4.64 (t, 2H), 6.38 (d, 1H), 6.80 (d, 1H), 6.99 (t, 1H), 7.10 (d, 1H), 7.28 (t, 2H), 7.62 (d, 3H), 7.75 (s, 1H), 8.38 (d, 1H), 9.38 (s, 1H); m/z 362.

Workup

  1. additionwas added to the residue
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 5 hours
  4. temperatureto cool
  5. washwashed with water
  6. extractionextracted with EtOAc
  7. customdried
  8. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-1c8437d4f60c4403bedbf5f122ef9d08
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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