2-Fluoroethyl bromide → 3,6-diethyl-N-[(1R,2S)-2-(2-fluoroethoxy)-2,3-dihydro-1H-inden-1-yl]-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine

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Reaction Steps

Following the general procedure of Example 13 Step 3 and making non-critical variations but substituting iodoethane with 1-bromo-2-fluoroethane and substituting (2S)-2-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]butan-1-ol with (1R,2S)-1-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol (240 mg, 0.54 mmol) gave 260 mg of a crude yellow paste. This material was purified by Biotage MPLC (40 g column, 25% ethyl acetate in heptane) to give 203 mg (65%) of 3,6-diethyl-N-[(1R,2S)-2-(2-fluoroethoxy)-2,3-dihydro-1H-inden-1-yl]-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine as an ivory foam. Rf 0.20 (25% ethyl acetate in heptane). IR (diffuse reflectance) 2966, 2932, 2875, 2857, 1562, 1551, 1482, 1389, 1309, 1248, 1232, 1203, 1183, 1118, 1033 cm−1. OAMS supporting ions at: ESI+490.2. Anal. Calcd for C30H36FN3O2: C, 73.59; H, 7.41; N, 8.58; F, 3.88. Found: C, 73.57; H, 7.65; N, 8.41.

Provenance & Evidence