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

HRID 2047117Notes

Reaction equation

HRID 2047117 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]4C([CH:20]=3)=CC=CC=4)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]([OH:30])=[O:29])[CH2:23][CH2:22]2)[C:3]=1[Br:31].[NH2:32]C1N2N=CC(C3C=NN(C)C=3)=C2N=C(C2CCN(CC(OC(C)(C)C)=O)CC2)C=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:20]=[N:32][N:13]([CH3:14])[CH:12]=3)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]([OH:30])=[O:29])[CH2:23][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 66735765tert-Butyl 2-(4-(7-amino-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetateHCID 66738335Tert-butyl 2-(4-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetate

Product 1

HCID 667332712-(4-(7-amino-6-bromo-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetic acid

Procedure

2-(4-(7-amino-6-bromo-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)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)piperidin-1-yl)acetic acid, but with tert-butyl 2-(4-(7-amino-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetate 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 mixture was reduced in vacuo and purified via reverse-phase preparatory HPLC to yield 2-(4-(7-amino-6-bromo-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)acetic acid as off-yellow solid. (m+H=434.19, retention time=2.25 min)

Workup

  1. custompurified via reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-ceba5b64474245968a5b118b9b101c32
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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