Ethyl 4-ethynylbenzoate → 4-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-N-methyl-benzamide

HRID 269361Notes

Reaction equation

HRID 269361 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19](I)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:33]=[CH:32][C:26]([C:27](OCC)=[O:28])=[CH:25][CH:24]=1)#[CH:22].[NH3:34].C1COCC1.[CH3:40]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19]([C:22]#[C:21][C:23]4[CH:33]=[CH:32][C:26]([C:27]([NH:34][CH3:40])=[O:28])=[CH:25][CH:24]=4)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 15540683Ethyl 4-ethynylbenzoateHCID 670008755-(4-Chloro-phenyl)-7-cyclopropyl-3-iodo-pyrazolo[1,5-a]pyrimidineHCID 86608128NH3 THF MeOH

Product 1

HCID 118522164-[5-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-N-methyl-benzamide

Procedure

The title compound was prepared by reacting 5-(4-chloro-phenyl)-7-cyclopropyl-3-iodo-pyrazolo[1,5-a]pyrimidine (example C.5 step 4) (792 mg, 2.0 mmol) and ethyl 4-ethynyl-benzoate (350 mg, 2.0 mmol) according to general procedure II, and subsequently, heating the suspension of the obtained product in 1 M NH3/THF-MeOH (1:1) to 60° C. for 75 h. Obtained as a yellow solid (6 mg, 14%). MS (ISP) 427.3 [(M+H)+]; mp 214-216° C.

Workup

  1. temperaturesubsequently, heating

Sources & evidence

ORD record
ord-0c62d099e3134924a75618482ff49d29
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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