Pyridine → HCID 59468608, compound

HRID 1012176Notes

Reaction equation

HRID 1012176 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].OC(C(F)(F)F)=O.[NH2:13][C:14]1[S:18][C:17]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[N:20]=2)=[CH:16][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[C:28]1([CH3:32])[CH:29]=[CH:30][CH:31]=[C:26]([NH:25][C:21]2[N:20]=[C:19]([C:17]3[S:18][C:14]([NH:13][C:1](=[O:4])[CH2:2][CH3:3])=[CH:15][CH:16]=3)[CH:24]=[CH:23][N:22]=2)[CH:27]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 86612624HCID 86612624, compound

Product 1

HCID 59468608HCID 59468608, compoundYield 39.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of propionyl chloride (4.85 uL, 0.055 mmol) in DCM (100 uL) was added dropwise to a DCM solution (400 uL) of [4-(5-aminothiophen-2-yl)-pyrimidin-2-yl]-m-tolyl-amine TFA salt (20 mg, 0.050 mmol), followed by addition of pyridine (8.9 uL, 0.11 mmol). After 16 hours, the reaction was diluted with DMSO and prep purified to afford N-[5-(2-m-tolylamino-pyrimidin-4-yl)-thiophene-2-yl]-propionamide (6.7 mg, 39.6%). The major impurity was the TFA amide. 1H NMR (500 MHz, DMSO-d6) δ 1.11 (t, J=7 Hz, 3H), 2.33 (s, 3H), 2.38 (q, J=7 Hz, 2H), 6.69 (d, J=4 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 7.12 (t, J=8 Hz, 1H), 7.18 (d, J=5.5 Hz, 1H), 7.50 (d, J=8 Hz, 1H), 7.72 (d, J=4 Hz, 1H), 7.81 (s, 1H), 8.33 (d, J=5.5 Hz, 1H), 9.44 (s, 1H), 11.38 (s, 1H). MS: m/z 339 (M+H+).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-e7e72cb26fcc4bdab889f28abae1be9a
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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