1,2-Dichloroethane → HCID 59635511, compound

HRID 383701Notes

Reaction equation

HRID 383701 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[CH:10][C:9]([C:12]3[S:16][C:15]([C:17]([OH:19])=O)=[CH:14][CH:13]=3)=[N:8][C:7]=12)=[O:2].C1[CH:21]=[CH:22][C:23]2N(O)N=[N:26][C:24]=2C=1.C(N(CC)CC)C.C1(CN)CC1.C(Cl)CCl>O.CN(C=O)C>[CH:23]1([CH2:24][NH:26][C:17]([C:15]2[S:16][C:12]([C:9]3[CH:10]=[CH:11][N:6]4[N:5]=[CH:4][C:3]([CH:1]=[O:2])=[C:7]4[N:8]=3)=[CH:13][CH:14]=2)=[O:19])[CH2:21][CH2:22]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 596355065-(3-Formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid

Product 1

HCID 59635511HCID 59635511, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the reaction flask, 5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid (43 mg, 0.16 mmol) was added to DMF (1 mL) along with HOBt (25 mg, 0.16 mmol), triethylamine (22 uL, 0.16 mmol) and cyclopropylmethylamine (11 mg, 0.16 mmol). The reaction mixture was stirred at room temperature for 5 minutes then EDC (31 mg, 0.16 mmol) was added. The reaction was allowed to stir for an additional 2 hours then diluted with water and filtered. The recovered solid was washed with more water followed by ethanol. The product, N-(cyclopropylmethyl)-5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide, was collected as a solid in 19% yield. LCMS (M+1=327)

Workup

  1. stirringto stir for an additional 2 hours
  2. filtrationfiltered
  3. washThe recovered solid was washed with more water
  4. customThe product, N-(cyclopropylmethyl)-5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide, was collected as a solid in 19% yield

Sources & evidence

ORD record
ord-d762ce8cc9ee4b349d43f06240cee033
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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