HCID 66733403, compound → HCID 58173338, compound

HRID 2047202Notes

Reaction equation

HRID 2047202 reaction equation
BrC1C(C2CCNCC=2)=NC2N(N=CC=2C2C=NC3C(C=2)=CC=CC=3)C=1N.[Br:28][C:29]1[C:30]([C:65]2[CH2:70][CH2:69][CH:68]([C:71]3[CH:72]=[N:73][N:74](COCC[Si](C)(C)C)[CH:75]=3)[CH2:67][CH:66]=2)=[N:31][C:32]2[N:33]([N:52]=[CH:53][C:54]=2[C:55]2[CH:56]=[N:57][C:58]3[C:63]([CH:64]=2)=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:34]=1[N:35](COCC[Si](C)(C)C)COCC[Si](C)(C)C.C[Si](C)(C)CCOCN(COCC[Si](C)(C)C)C1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCN(C(OC(C)(C)C)=O)CC=2)C=1>>[NH:73]1[CH:72]=[C:71]([CH:68]2[CH2:69][CH2:70][C:65]([C:30]3[C:29]([Br:28])=[C:34]([NH2:35])[N:33]4[N:52]=[CH:53][C:54]([C:55]5[CH:56]=[N:57][C:58]6[C:63]([CH:64]=5)=[CH:62][CH:61]=[CH:60][CH:59]=6)=[C:32]4[N:31]=3)=[CH:66][CH2:67]2)[CH:75]=[N:74]1

Participants

4

Reactant 3

HCID 66733403HCID 66733403, compoundHCID 67494206HCID 67494206, compoundHCID 67494642HCID 67494642, compound

Product 1

HCID 58173338HCID 58173338, compound

Procedure

5-(4-(1H-pyrazol-4-yl)cyclohex-1-enyl)-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine was synthesized in a manner similar to the synthesis of 6-bromo-3-(quinolin-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine, but with 6-bromo-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)cyclohex-1-enyl)pyrazolo[1,5-a]pyrimidin-7-amine substituted for tert-Butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate. The reaction mixture was purified via reverse-phase preparatory HPLC to yield 5-(4-(1′-1-pyrazol-4-yl)cyclohex-1-enyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as yellow solid. (M+H=486.12, retention time=3.43 min.

Workup

  1. customThe reaction mixture was purified via reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-24f8fa0608ad40c98724f59d605bb6a6
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…