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

HRID 1063263Notes

Reaction equation

HRID 1063263 reaction equation
Br[CH2:2][CH2:3][F:4].[CH2:5]([C:7]1[C:8]([NH:27][C@@H:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][C@@H:29]2[OH:37])=[N:9][C:10]([CH2:25][CH3:26])=[C:11]([C:13]2[C:22]([O:23][CH3:24])=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=2)[N:12]=1)[CH3:6]>>[CH2:5]([C:7]1[C:8]([NH:27][C@@H:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][C@@H:29]2[O:37][CH2:2][CH2:3][F:4])=[N:9][C:10]([CH2:25][CH3:26])=[C:11]([C:13]2[C:22]([O:23][CH3:24])=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=2)[N:12]=1)[CH3:6]

Participants

3

Reactant 2

HCID 129822-Fluoroethyl bromideHCID 23401193(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

Product 1

HCID 234011953,6-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-amineYield 65%

Procedure

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.

Workup

  1. customgave 260 mg of a crude yellow paste
  2. customThis material was purified by Biotage MPLC (40 g column, 25% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c4cb917c1561419c8d3d626f88153399
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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