Ethanol → 5-(3-chlorobenzylamino)-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamide

HRID 474322Notes

Reaction equation

HRID 474322 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:12])=[C:4]2[CH:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH2:25].C(N(CC)C(C)C)(C)C.C(O)C>CO.ClCCl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH:25][C:2]1[N:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:12])=[C:4]2[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 77802Benzenemethanamine, 3-chloro-HCID 81531DiisopropylethylamineHCID 866614385-chloro-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamide

Product 1

HCID 666775365-(3-chlorobenzylamino)-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamideYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamide (28 mg, 0.09 mM, 1.0 equiv), 3-chlorobenzylamine (28 mg, 0.18 mM, 2.0 equiv), N,N-diisopropylethylamine (26 mg, 0.18 mM, 2.0 equiv) and 2 mL of ethanol were microwaved at 120° C. for 10 minutes. TLC (95:5 dichloromethane:methanol) showed reaction complete. The reaction mixture was cooled, the crystalline product collected by filtration, washed with cold ethanol and air dried to yield 29.7 mg (77%) of 5-(3-chlorobenzylamino)-N-cyclohexylpyrazolo[1,5-c]pyrimidine-3-carboxamide. LCMS (ESI) m+H=384.2; 1H NMR (400 MHz, DMSO-d6) δ: 8.61 (overlapping d and t, 2H), 8.06 (s, 1H), 7.60 (d, 1H), 7.4-7.25 (m, 4H), 6.49 (d, 1H), 3.70 (m, 1H), 1.75-1.5 (m, 5H), 1.4-0.8 (m, 5H).

Workup

  1. customreaction complete
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe crystalline product collected by filtration
  4. washwashed with cold ethanol and air
  5. customdried

Sources & evidence

ORD record
ord-8f2868dbc553423ea83c74cdcf8e87c5
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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