HCID 58173379, compound → HCID 58173414, compound

HRID 2047187Notes

Reaction equation

NC1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCN([C:27]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)=[O:28])CC=2)C=1Br.[Cl:35][C:36]1[C:37]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)=[N:38][C:39]2[N:40]([N:43]=[CH:44][C:45]=2[C:46]2[CH:47]=[N:48][C:49]3[C:54]([CH:55]=2)=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:41]=1[NH2:42].BrC1C(C2CCNCC=2)=NC2N(N=CC=2C2C=NC3C(C=2)=CC=CC=3)C=1N>>[NH2:42][C:41]1[N:40]2[N:43]=[CH:44][C:45]([C:46]3[CH:47]=[N:48][C:49]4[C:54]([CH:55]=3)=[CH:53][CH:52]=[CH:51][CH:50]=4)=[C:39]2[N:38]=[C:37]([N:56]2[CH2:57][CH2:58][N:59]([C:27]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)=[O:28])[CH2:60][CH2:61]2)[C:36]=1[Cl:35]

Participants

Reactant 3

HCID 58173379HCID 58173379, compound

HCID 66733403HCID 66733403, compound

HCID 66733508HCID 66733508, compound

Product 1

HCID 58173414HCID 58173414, compound

Procedure

(4-(7-Amino-6-chloro-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)(thiophen-2-yl)methanone was synthesized in a manner similar to the synthesis of (4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone, but with 6-chloro-5-(piperazin-1-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine substituted for 6-bromo-3-(quinolin-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine. The reaction was purified via reverse-phase preparatory HPLC to yield (4-(7-amino-6-chloro-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)(thiophen-2-yl)methanone as yellow solid. (M+H=490.19, retention time=3.75 min).

Workup

customThe reaction was purified via reverse-phase preparatory HPLC

Sources & evidence

ORD record: ord-e4a358e5adc24e11a706ccd19ebd9c4e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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