Cyclohexylamine → 5-chloro-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamide

HRID 474321Notes

Reaction equation

HRID 474321 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11](Cl)=[O:12])=[C:4]2[CH:3]=1.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:20][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:12])=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 866614395-Chloropyrazolo[1,5-c]pyrimidine-3-carbonyl chloride

Product 1

HCID 866614385-chloro-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude 5-chloropyrazolo[1,5-c]pyrimidine-3-carbonyl chloride (200 mg, 0.9 mM, 1.0 equiv) in 15 mL of dichloromethane was added cyclohexylamine (400 ul, 4.0 mM, 4 equiv). The reaction mixture was stirred for 15 minutes then quenched with 0.4 mL of acetic acid. The reaction mixture was concentrated under reduced pressure and the residue partitioned between water and dichloromethane. The dichloromethane phase was concentrated, and the crude product purified by flash chromatography on silica gel (97:3 dichloromethane:methanol) to yield 310 mg (100%) of 5-chloro-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamide. LCMS (ESI) m+H=279.1; 1H NMR (400 MHz, CDCl3) δ: 8.66 (s, 1H), 8.65 (d, 1H), 7.47 (d (broad exchangeable) 1H), 6.93 (d, 1H), 4.08 (m, 1H), 2.02 (m, 2H), 1.80 (m, 2H), 1.62 (m, 1H), 1.40 (m, 5H).

Workup

  1. customthen quenched with 0.4 mL of acetic acid
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue partitioned between water and dichloromethane
  4. concentrationThe dichloromethane phase was concentrated
  5. customthe crude product purified by flash chromatography on silica gel (97:3 dichloromethane:methanol)

Sources & evidence

ORD record
ord-79952759a8004510b6356f8438a3c7b6
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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