Diisopropylethylamine → HCID 178423950, compound

HRID 1478684Notes

Reaction equation

HRID 1478684 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH:19]([NH2:21])[CH3:20])[CH:5]=[C:6]([F:8])[CH:7]=1.Br[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][NH:27]2.C(N(CC)C(C)C)(C)C>C(O)C.CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[C:14]([CH3:18])=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH:19]([NH:21][C:23]2[N:31]=[CH:30][N:29]=[C:28]3[C:24]=2[N:25]=[CH:26][NH:27]3)[CH3:20])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 583793101-[3-(3,5-Difluorophenyl)-5-methylimidazo[1,2-a]pyridin-2-yl]ethanamineHCID 178419477HCID 178419477, compound

Product 1

HCID 178423950HCID 178423950, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 1-[3-(3,5-difluorophenyl)-5-methylimidazo[1,2-a]pyridin-2-yl]ethanamine (40 mg, 0.14 mmol), 6-bromo-9H-purine [Aldrich, 104981] (33 mg, 0.17 mmol), and N,N-diisopropylethylamine (29 μL, 0.17 mmol) in ethanol (1.6 mL) was heated at 90° C. for 18 h. The reaction mixture was diluted with methanol and purified by preparative LCMS to give the desired product (33 mg, 58%) as a white solid. LCMS for C21H18F2N7 (M+H)+: m/z=406.1. 1H NMR (400 MHz, CD3OD): δ 8.12 (s, 1 H), 8.03 (br s, 1 H), 7.49 (d, J=9.0 Hz, 1 H), 7.25 (dd, J=9.0, 6.8 Hz, 1 H), 7.21-7.18 (m, 1 H), 7.00-6.94 (m, 2 H), 6.66 (d, J=6.8 Hz, 1 H), 5.44 (br s, 1 H), 2.15 (s, 3 H), 1.69 (d, J=7.0 Hz, 3 H).

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-8522233bf7cd4dc2afe29c00973976f9
Source dataset
uspto-grants-2016_08
Patent number
US09403847B2

Reaction notes

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