1-[4-(2-Aminopyrimidin-5-yl)phenyl]cyclopropanecarboxylic acid → HCID 67225167, compound

HRID 1257909Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([OH:19])=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][N:3]=1.Cl[CH:21]([C:24]1([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[N:33]=[CH:32][CH:31]=[CH:30]3)[CH2:26][CH2:25]1)[CH:22]=O>C(O)C>[N:33]1[C:34]2[C:29](=[CH:28][C:27]([C:24]3([C:21]4[N:7]5[CH:6]=[C:5]([C:8]6[CH:9]=[CH:10][C:11]([C:14]7([C:17]([OH:19])=[O:18])[CH2:16][CH2:15]7)=[CH:12][CH:13]=6)[CH:4]=[N:3][C:2]5=[N:1][CH:22]=4)[CH2:26][CH2:25]3)=[CH:36][CH:35]=2)[CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[4-(2-aminopyrimidin-5-yl)phenyl]cyclopropanecarboxylic acid (0.22 g, 0.86 mmol) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (0.21 g, 0.86 mmol) in ethanol (8 mL) was stirred at 100° C. overnight. The reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product (0.12 g, 31%). LCMS: (M+H)=447.1.

Workup

customThe reaction mixture was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record: ord-214832c095b64822a77e78b10b739516
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461330B2

Reaction notes

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