Triethylamine → HCID 89826106, compound

HRID 2206845Notes

Reaction equation

HRID 2206845 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([NH2:14])=[O:13])=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[CH3:15][C@H:16]1[CH2:24][C:23]2[C:18](=[CH:19][C:20]([CH3:25])=[CH:21][CH:22]=2)[C@@H:17]1[NH2:26].C(N(CC)CC)C>CN(C)C(=O)C>[Cl:1][C:2]1[C:3]([C:12]([NH2:14])=[O:13])=[N:4][C:5]([NH:26][C@H:17]2[C:18]3[C:23](=[CH:22][CH:21]=[C:20]([CH3:25])[CH:19]=3)[CH2:24][C@@H:16]2[CH3:15])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16764602HCID 16764602, compoundHCID 671406111351564-23-2

Product 1

HCID 89826106HCID 89826106, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.30 g (1.27 mmol) of 5-chloro-2-(methylsulfonyl)pyrimidine-4-carboxamide, 0.25 g (1.53 mmol) of (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-indene-1-amine and 0.28 g (2.54 mmol) of triethylamine in 1.5 ml of N,N-dimethylacetamide are heated in a closed cuvette in the microwave at 120° C. for 45 minutes (Biotage Initiator, http://www.biotage.com/DynPage.aspx?id=22001). The crude mixture obtained in this manner is applied to silica gel and purified by column chromatography using the mobile phase heptane/ethyl acetate. Concentration gives initially 0.07 g of 5-chloro-2-{[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]amino}pyrimidine-4-carboxamide (wax-like) and then 0.252 g of 5-{[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]amino}-2-(methylsulfonyl)pyrimidine-4-carboxamide (yield 52% at a purity of 95%).

Workup

  1. customThe crude mixture obtained in this manner
  2. custompurified by column chromatography
  3. concentrationConcentration

Sources & evidence

ORD record
ord-96bc9bcd1d294415a1a58693bdac44a3
Source dataset
uspto-grants-2016_06
Patent number
US09375002B2

Reaction notes

Loading…