2-Bromopyridine → 5-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxy-1-pyridin-2-ylpyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HRID 1297305Notes

Reaction equation

HRID 1297305 reaction equation
C(O[C@H]1CN(C2N=CC=CN=2)C[C@H]1NC1C(CC)=NC([C:24]2[C:25](C)=[N:26][C:27](OC)=[CH:28][CH:29]=2)=C(CC)N=1)C.BrC1C=CC=CN=1.[CH3:42][N:43]([CH3:70])[C:44]1[N:49]=[CH:48][C:47]([C:50]2[N:51]=[C:52]([CH2:67][CH3:68])[C:53]([NH:58][C@H:59]3[C@@H:63]([O:64][CH2:65][CH3:66])[CH2:62][NH:61][CH2:60]3)=[N:54][C:55]=2[CH2:56][CH3:57])=[C:46]([CH3:69])[CH:45]=1>>[CH3:70][N:43]([CH3:42])[C:44]1[N:49]=[CH:48][C:47]([C:50]2[N:51]=[C:52]([CH2:67][CH3:68])[C:53]([NH:58][C@H:59]3[C@@H:63]([O:64][CH2:65][CH3:66])[CH2:62][N:61]([C:25]4[CH:24]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:60]3)=[N:54][C:55]=2[CH2:56][CH3:57])=[C:46]([CH3:69])[CH:45]=1

Participants

4

Reactant 3

HCID 79732-BromopyridineHCID 11374683N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amineHCID 58914568HCID 58914568, compound

Product 1

HCID 113973755-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxy-1-pyridin-2-ylpyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Procedure

Following the procedure for the preparation of N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine but substituting 2-bromo pyridine and 5-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ) 8.19, 7.99, 7.47, 6.58, 6.46, 6.41, 5.25, 4.90, 4.25, 4.02, 3.80–3.72, 3.55, 3.40, 3.13, 2.70, 2.54, 2.12, 1.29, 1.16; IR (liq.) 2969, 2930, 2871, 2414 (w), 1941 (w), 1602 (s), 1558 (s), 1490 (s), 1474 (s), 1443 (s), 1395 (s), 1374, 1166, 1124, 770 cm−1 HRMS (ESI) calcd for C27H37N7O+H1 476.3138. found 476.3134.

Sources & evidence

ORD record
ord-c3185e445d254b85a206bb73254ca34e
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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