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

HRID 1824052Notes

Reaction equation

HRID 1824052 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[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])=NC=1CC.[CH3:32][N:33]([CH3:62])[C:34]1[N:39]=[CH:38][C:37]([C:40]2[N:41]=[C:42]([CH2:59][CH3:60])[C:43]([NH:48][C@@H]3C4C(=CC=CC=4)C[C@@H]3O)=[N:44][C:45]=2[CH2:46][CH3:47])=[C:36]([CH3:61])[CH:35]=1>>[CH3:62][N:33]([CH3:32])[C:34]1[N:39]=[CH:38][C:37]([C:40]2[N:41]=[C:42]([CH2:59][CH3:60])[C:43]([NH:48][C@@H:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][C@@H:19]3[O:27][CH2:28][CH3:29])=[N:44][C:45]=2[CH2:46][CH3:47])=[C:36]([CH3:61])[CH:35]=1

Participants

3

Reactant 2

HCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 58583251(1R,2S)-1-({5-[6-(dimethylamino)-4-methylpyridin-3-yl]-3,6-diethylpyrazin-2-yl}amino)-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 235936805-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-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 (1R,2S)-1-({5-[6-(dimethylamino)-4-methylpyridin-3-yl]-3,6-diethylpyrazin-2-yl}amino)-2,3-dihydro-1H-inden-2-ol and making non-critical variations provided the title compound as a light golden amorphous solid. IR (diffuse reflectance) 3446, 2969, 2931, 2893, 2874, 1604, 1562, 1517, 1487, 1392, 1372, 1208, 1174, 1123, 1089 cm−1; OAMS supporting ions at: ESI+ 446.3; MS (EI) m/z 445 (M+); HRMS (FAB) calcd for C27H35N5O+H1 446.2920, found 446.2915. [α]25D=−89 (c 0.47, methylene chloride); Anal. Calcd for C27H35N5O: C, 72.78; H, 7.92; N, 15.72. Found: C, 72.58; H, 7.94; N, 15.59.

Sources & evidence

ORD record
ord-7d7ced502ebb44979cb24142b3d411c3
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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