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

HRID 2047107Notes

Reaction equation

HRID 2047107 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]N(CC(O)=O)[CH2:23][CH2:22]2)[C:3]=1[Br:31].C[Si](C)(C)CCOC[N:38](COCC[Si](C)(C)C)[C:39]1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCC(CC#N)C2)[CH:40]=1.NC1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCN(CC(OC(C)(C)C)=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][CH:23]([CH2:40][C:39]#[N:38])[CH2:22]2)[C:3]=1[Br:31]

Participants

4

Reactant 3

HCID 581735492-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetic acidHCID 667334062-(3-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopentyl)acetonitrileHCID 66738335Tert-butyl 2-(4-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetate

Product 1

HCID 581734792-(3-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopentyl)acetonitrile

Procedure

2-(3-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopentyl)acetonitrile 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)piperidin-1-yl)acetic acid, but with 2-(3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopentyl)acetonitrile substituted for tert-butyl 2-(4-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetate. The reaction was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield 2-(3-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopentyl)acetonitrile as a yellow solid. (m+H=447.22, retention time=3.99 min).

Workup

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

Sources & evidence

ORD record
ord-50e4663e971b417b9130b21d6f8f0b7b
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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