2-Fluoroethyl bromide → 5-(2-chloro-4-methoxyphenyl)-3,6-diethyl-N-[(1R,2S)-2-(2-fluoroethoxy)-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine

HRID 1612127Notes

Reaction equation

HRID 1612127 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2OCC)=NC=1CC.[Cl:32][C:33]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[C:41]1[N:42]=[C:43]([CH2:60][CH3:61])[C:44]([NH:49][C@@H:50]2[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH2:52][C@@H:51]2[OH:59])=[N:45][C:46]=1[CH2:47][CH3:48].Br[CH2:63][CH2:64][F:65]>>[Cl:32][C:33]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[C:41]1[N:42]=[C:43]([CH2:60][CH3:61])[C:44]([NH:49][C@@H:50]2[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH2:52][C@@H:51]2[O:59][CH2:63][CH2:64][F:65])=[N:45][C:46]=1[CH2:47][CH3:48]

Participants

4

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 58631222(1R,2S)-1-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 102172975-(2-chloro-4-methoxyphenyl)-3,6-diethyl-N-[(1R,2S)-2-(2-fluoroethoxy)-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting (1R,2S)-1-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol and 1-bromo-2-fluoroethane and making non-critical variations provided the title compound as a pale yellow semi-solid. IR (diffuse reflectance) 2970, 1604, 1564, 1481, 1439, 1391, 1286, 1228, 1204, 1182, 1123, 1109, 1044, 876, 750 cm−1; OAMS supporting ions at: ESI+ 470.1; MS (EI) m/z 469 (M+); HRMS (FAB) calcd for C26H29CLFN3O2+H1 470.2010, found 470.2013. [α]25D=−82 (c 0.39, methylene chloride); Anal. Calcd for C26H29ClFN3O2: C, 66.45; H, 6.22; N, 8.94. Found: C, 66.41; H, 6.37; N, 8.84.

Sources & evidence

ORD record
ord-fe40c33e82c64dd693c22eba56133b89
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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