Triethylamine → HCID 66851991, compound

HRID 1668545Notes

Reaction equation

HRID 1668545 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH2:17])[N:11]=2)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=2)[C:3]=1[C:28]#[N:29].C(N(CC)CC)C.Br[CH2:38][CH2:39][C:40](Cl)=[O:41]>CS(C)=O.C(Cl)(Cl)Cl>[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:4]2[C:3]([C:28]#[N:29])=[C:2]([NH2:1])[N:7]=[C:6]([S:8][CH2:9][C:10]3[N:11]=[C:12]([CH2:16][NH:17][C:40](=[O:41])[CH:39]=[CH2:38])[CH:13]=[CH:14][CH:15]=3)[N:5]=2)=[CH:19][CH:20]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 84944Propanoyl chloride, 3-bromo-HCID 66853748HCID 66853748, compound

Product 1

HCID 66851991HCID 66851991, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Procedure

The compound of Example 32 (0.5 g) and triethylamine (0.3 mL) was dissolved in 5 mL of DMSO, to the solution at ice temperature added 0.17 g of 3-bromopropionyl chloride, and the mixture was stirred for 30 minutes. The reaction mixture was diluted with chloroform, washed with water (twice) and brine (once), and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed, and the resulting crude crystal was washed with diethyl ether to give 0.12 g of N-{6-[4-(4-acetylaminophenyl)-6-amino-5-cyanopyrimidin-2-ylsulfanylmethyl]pyridin-2-ylmethyl}acryl-amide as a white powder.

Workup

  1. washwashed with water (twice) and brine (once), and the organic layer
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. customThe solvent was removed
  4. washthe resulting crude crystal was washed with diethyl ether

Sources & evidence

ORD record
ord-82d530aa766e462b9ae9f1d61a0a6f15
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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