Bromomethylcyclopropane → N-[(1R,2S)-2-(cyclopropylmethoxy)-2,3-dihydro-1H-inden-1-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine

HRID 1612119Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:30][CH3:31])[C:12]([NH:17][C@@H:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2[O:27][CH2:28][CH3:29])=[N:13][C:14]=1[CH2:15][CH3:16].Br[CH2:33][CH:34]1CC1>>[CH:29]1([CH2:28][O:27][C@H:19]2[CH2:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:18]2[NH:17][C:12]2[C:11]([CH2:30][CH3:31])=[N:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:14]([CH2:15][CH3:16])[N:13]=2)[CH2:34][CH2:33]1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine

Product 1

HCID 10128040N-[(1R,2S)-2-(cyclopropylmethoxy)-2,3-dihydro-1H-inden-1-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-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 (bromomethyl)cyclopropane and making non-critical variations provided the title compound as a yellow amorphous solid. IR (liq.) 3442, 2971, 2935, 2874, 1565, 1552, 1498, 1471, 1393, 1206, 1184, 1101, 1077, 1021, 740 cm−1; OAMS supporting ions at: ESI+ 481.8; MS (EI) m/z 481 (M+); HRMS (FAB) calcd for C27H29CL2N3O +H1 482.1766, found 482.1775. [α]25D=−65 (c 0.73, methylene chloride); Anal. Calcd for C27H29Cl2N3O: C, 67.22; H, 6.06; N, 8.71. Found: C, 67.15; H, 6.08; N, 8.66.

Sources & evidence

ORD record: ord-30eacabb7f4a41e2ab61cb40543b608e
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992087B2

Reaction notes

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