HCID 67223833, compound → 2,3-Difluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid

HRID 500267Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:17])[C:9]=2[F:18])=[CH:4][N:3]=1.Cl[CH:20]([C:30]1([C:33]2[CH:34]=[C:35]3[C:40](=[CH:41][CH:42]=2)[N:39]=[CH:38][CH:37]=[CH:36]3)[CH2:32][CH2:31]1)[CH:21](N1C(=O)CCC1=O)O>C(O)C>[F:17][C:10]1[C:9]([F:18])=[C:8]([C:5]2[CH:6]=[N:7][C:2]3[N:3]([C:20]([C:30]4([C:33]5[CH:34]=[C:35]6[C:40](=[CH:41][CH:42]=5)[N:39]=[CH:38][CH:37]=[CH:36]6)[CH2:32][CH2:31]4)=[CH:21][N:1]=3)[CH:4]=2)[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(2-aminopyrimidin-5-yl)-2,3-difluorobenzoic acid (15 mg, 0.060 mmol) and 1-[2-chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione (20 mg, 0.058 mmol) in ethanol (1.0 mL) was stirred at 100° C. overnight. The reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product (9 mg, 40%). LCMS: (M+H)=443.0.

Workup

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

Sources & evidence

ORD record: ord-8c14c4788e8f4197a4ef548dd0d2a3e5
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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