2-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid → 2-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetonitrile

HRID 2047106Notes

Reaction equation

HRID 2047106 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][CH2:25][CH:24]([CH2:27][C:28](O)=O)[CH2:23][CH2:22]2)[C:3]=1[Br:31].C[Si](C)(C)CCOC[N:38](COCC[Si](C)(C)C)C1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCCC([CH2:64][C:65]([O:67]CC)=[O:66])C2)C=1.C[Si](C)(C)CCOCN(COCC[Si](C)(C)C)C1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCC(CC(OCC)=O)CC2)C=1>>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][CH2:25][CH2:24][CH:23]([CH2:64][C:65]([OH:67])=[O:66])[CH2:22]2)[C:3]=1[Br:31].[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][CH2:25][CH:24]([CH2:27][C:28]#[N:38])[CH2:23][CH2:22]2)[C:3]=1[Br:31]

Participants

5

Reactant 3

HCID 581734442-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acidHCID 66738318HCID 66738318, compoundHCID 67494375Ethyl 2-(3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

Product 2

HCID 469447502-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetonitrileHCID 581735002-(3-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid

Procedure

2-(3-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid was synthesized in a manner similar to the synthesis of 2-(4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetic acid, but with ethyl 2-(3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate substituted for ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate. The reaction was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield 2-(4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetonitrile as a four-isomer mixture. (m+H=480.1, retention time=3.51 min)

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified via reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-6f4744ecc1c64e38a11d6f67a74712f5
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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