Acetyl chloride → HCID 69310114, compound

HRID 2375317Notes

Reaction equation

HRID 2375317 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:11]=[C:10]([C:12](=[C:15]2[NH:19][C:18]([CH2:20][CH3:21])=[CH:17][S:16]2)[C:13]#[N:14])[CH:9]=[CH:8][N:7]=1.CCN(CC)CC.[C:29](Cl)(=[O:31])[CH3:30]>CC(N(C)C)=O>[C:13]([C:12](=[C:15]1[NH:19][C:18]([CH2:20][CH3:21])=[CH:17][S:16]1)[C:10]1[CH:9]=[CH:8][N:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:29](=[O:31])[CH3:30])[N:11]=1)#[N:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67068562HCID 67068562, compound

Product 1

HCID 69310114HCID 69310114, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of {2-[(3-aminopropyl)amino]pyrimidin-4-yl}(4-ethyl-1,3-thiazol-2(3H)-ylidene)acetonitrile (165 mg, 0.37 mmol) in DMA (3 mL) were added and Et3N (0.048 mL, 0.37 mmol) and acetyl chloride (0.04 mL, 0.46 mmol) at 0° C. The resulting solution was stirred at 0° C. for 3 h. The solvent was evaporated under reduced pressure (Genevac) affording the title compound as a crude yellow solid. HPLC (max plot) 92%. The solid was taken up in DCM and an excess TFA was added. The yellow precipitate formed after addition of ether was filtered off and washed with ether (×3) then dried under vacuum at 40° C. After purification by preparative HPLC then lyophilization, 148 mg of the title compound was obtained as a TFA salt (yellow powder, Y=87.3%)

Workup

  1. customat 0° C
  2. customThe solvent was evaporated under reduced pressure (Genevac)

Sources & evidence

ORD record
ord-0ce535582a014d6497f59da470075958
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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