Morpholine → HCID 58313738, compound

HRID 624714Notes

Reaction equation

HRID 624714 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[O:15])=[C:9]3[N:8]=[C:7]([C:16]3[CH:17]=[CH:18][C:19]([F:25])=[C:20]([CH:24]=3)[C:21](O)=[O:22])[CH:6]=2)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[O:15])=[C:9]3[N:8]=[C:7]([C:16]3[CH:17]=[CH:18][C:19]([F:25])=[C:20]([C:21]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[O:22])[CH:24]=3)[CH:6]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58313810HCID 58313810, compound

Product 1

HCID 58313738HCID 58313738, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-2-fluorobenzoic acid (75 mg, 0.22 mmol 0 in DMF (3 mL) was added EDCI (46 mg, 0.24 mmol), HOBt (33 mg, 0.24 mmol), and morpholine (21 mg, 0.24 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed 1× with saturated sodium bicarbonate, 2× with brine, dried over MgSO4, filtered and evaporated to dryness to provide 92 mg of 7-(cyclopropylamino)-5-(4-fluoro-3-(morpholine-4-carbonyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. LCMS (M+1=410)

Workup

  1. washwashed 1× with saturated sodium bicarbonate, 2× with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0e466a75d30149629ce8eec98bc70ea5
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

Loading…