Diisopropylethylamine → HCID 178463542, compound

HRID 717824Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[N:4]([CH:18]=[N:19][CH:20]=2)[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[C:6]([CH:8]([NH2:10])[CH3:9])[CH:7]=1.Br[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[N:24]=[CH:25][NH:26]2.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:1][C:2]1[C:3]2[N:4]([CH:18]=[N:19][CH:20]=2)[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[C:6]([CH:8]([NH:10][C:22]2[N:30]=[CH:29][N:28]=[C:27]3[C:23]=2[N:24]=[CH:25][NH:26]3)[CH3:9])[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

1-[8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-yl]ethanamine (23 mg, 79 μmol), 6-bromo-9H-purine (32 mg, 0.16 mmol, Aldrich 104981) and N,N-diisopropylethylamine (69 μL, 0.40 mmol) were stirred in ethanol (1.0 mL) and heated to 130° C. for 30 minutes in a microwave. The mixture was evaporated and the resultant residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product as a racemic mixture (10 mg, 30%). LCMS calculated for C20H16ClFN7 (M+H)+: m/z=408.1. found: 408.0. 1H NMR (300 MHz, DMSO-d6): δ 8.09 (m, 3H), 8.65 (m, 3H), 7.42 (m, 4H), 5.02 (br s, 1H), 3.30 (m, 1H), 1.42 (m, 3H).

Workup

customThe mixture was evaporated
customthe resultant residue was purified on RP-HPLC (XBridge C18 column
washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record: ord-2321fc6841c64a83b425770ac8c7a853
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193721B2

Reaction notes

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