2-Chloro-1,1-diethoxyethane → HCID 57977403, compound

HRID 1866091Notes

Reaction equation

HRID 1866091 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[CH3:13])=[C:6]([NH:14][CH:15]([CH3:19])[CH:16]([CH3:18])[CH3:17])[N:5]2[N:20]=[CH:21][C:22]([C:23]([NH2:25])=[O:24])=[C:4]2[N:3]=1.[CH2:26](OC(OCC)CCl)[CH3:27]>C(O)C>[Cl:1][C:2]1[C:7]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[CH3:13])=[C:6]([NH:14][CH:15]([CH3:19])[CH:16]([CH3:18])[CH3:17])[N:5]2[N:20]=[CH:21][C:22]([C:23]3[O:24][CH:26]=[CH:27][N:25]=3)=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 121282-Chloro-1,1-diethoxyethaneHCID 57977430HCID 57977430, compound

Product 1

HCID 57977403HCID 57977403, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

0.95 g (2.5 mmol) of 5-chloro-7-(1,2-dimethylpropylamino)-6-(3-methylthiophen-2-yl)pyrazolo-[1,5-α]pyrimidine-3-carboxamide was dissolved in 25 ml of ethanol, and 1.0 g (6.5 mmol) of chloroacetaldehyde diethyl acetal was added. The mixture was stirred for 3 hours at 120° C. and 15 bar in a microwave oven (200 W). The reaction mixture was then concentrated under reduced pressure, and the residue that remained was chromatographed on silica gel using a mixture of cyclohexane:ethyl acetate=1:1. This gave 0.3 g of [5-chloro-6-(3-methylthiophen-2-yl)-3-oxazol-2-yl-pyrazolo[1,5-α]pyrimidin-7-yl](1,2-dimethylpropyl)amine (logPs=4.3; content according to HPLC: 98%)

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue that remained was chromatographed on silica gel using
  3. additiona mixture of cyclohexane

Sources & evidence

ORD record
ord-b1fd0e6d87d6420e8021b501525bda1e
Source dataset
uspto-grants-2009_12
Patent number
US07629294B2

Reaction notes

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