Diisopropylethylamine → HCID 178431860, compound

HRID 58298Notes

Reaction equation

[NH2:1][CH:2]([C:4]1[N:5]=[C:6]2[S:21][CH:20]=[C:19]([CH3:22])[N:7]2[C:8](=[O:18])[C:9]=1[C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)[CH3:3].Br[C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[N:26]=[CH:27][NH:28]2.C(N(CC)C(C)C)(C)C>C(O)C>[F:17][C:12]1[CH:11]=[C:10]([C:9]2[C:8](=[O:18])[N:7]3[C:19]([CH3:22])=[CH:20][S:21][C:6]3=[N:5][C:4]=2[CH:2]([NH:1][C:24]2[N:32]=[CH:31][N:30]=[C:29]3[C:25]=2[N:26]=[CH:27][NH:28]3)[CH3:3])[CH:15]=[C:14]([F:16])[CH:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 7-(1-aminoethyl)-6-(3,5-difluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.105 g, 0.327 mmol) (1st peak from Example 23, step 1 chiral separation), 6-bromo-9H-purine (0.117 g, 0.588 mmol), and N,N-diisopropylethylamine (0.114 mL, 0.654 mmol) in ethanol (1.5 mL) was heated at 110° C. overnight. The mixture was filtered, and the filtrate was purified on preparative-LCMS (XBridge C18 Column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH) to give the desired product (0.073 g, 51%). LCMS calculated for C20H16F2N7OS (M+H)+: m/z=440.1. Found: 440.0. 1H NMR (DMSO-d6, 500 MHz) δ 8.05 (2H, s), 7.34 (1H, br s), 7.18 (1H, m), 7.12 (2H, m), 6.84 (1H, s), 7.01 (1H, s), 5.07 (1H, m), 2.43 (3H, s), 1.31 (3H, d, J=7.0 Hz) ppm. 19F NMR (DMSO-d6, 376.3 MHz) δ −111 ppm.

Workup

filtrationThe mixture was filtered
customthe filtrate was purified on preparative-LCMS (XBridge C18 Column
washeluting with a gradient of acetonitrile/water containing 0.15% NH4OH)

Sources & evidence

ORD record: ord-4304fb8442ab4c5995a0eec76d0e40d9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434746B2

Reaction notes

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