Methyl chloroformate → HCID 10288558, compound

HRID 1824213Notes

Reaction equation

C(N1C[C@H](OCC)[C@H](NC2C(CC)=NC(C3C=CC(Cl)=CC=3Cl)=C(CC)N=2)C1)(=O)C.[Cl:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[C:40]1[N:41]=[C:42]([CH2:57][CH3:58])[C:43]([NH:48][C@H:49]2[C@@H:53]([O:54][CH2:55][CH3:56])[CH2:52][NH:51][CH2:50]2)=[N:44][C:45]=1[CH2:46][CH3:47].Cl[C:60]([O:62][CH3:63])=[O:61]>>[Cl:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[C:40]1[N:41]=[C:42]([CH2:57][CH3:58])[C:43]([NH:48][C@H:49]2[C@@H:53]([O:54][CH2:55][CH3:56])[CH2:52][N:51]([C:60]([O:62][CH3:63])=[O:61])[CH2:50]2)=[N:44][C:45]=1[CH2:46][CH3:47]

Participants

Reactant 3

HCID 6586Methyl chloroformate

HCID 102377515-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HCID 58583258N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine

Product 1

HCID 10288558HCID 10288558, compound

Procedure

Following the procedure for the preparation of N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine but substituting 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine and methyl chloroformate, and making non-critical variations provided the title compound as an oil: 1H NMR (DMSO-d6) δ 1.03–1.09, 1.16, 2.36, 2.67, 3.78, 3.51, 3.60, 3.69, 3.82, 4.15, 4.62, 5.95, 6.98, 7.11, 7.26; IR (diffuse reflectance) 2965 (s,b), 2937, 2351 (w), 2338 (w), 2213 (w), 2158 (w), 2059 (w), 1710 (s), 1568 (s), 1552, 1483 (s), 1456 (s), 1393 (s), 1287 (s), 1228, cm−1 HRMS (FAB) calcd for C23H30ClFN4O4+H 481.2018, found 481.2026. Anal. Calcd for C23H30ClFN4O4: C, 57.44; H, 6.29; N, 11.65; Cl, 7.37; F, 3.95. Found: C, 57.14; H, 6.46; N, 11.37.

Sources & evidence

ORD record: ord-e9198d49e81d45c891d25f7080a36d27
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041672B2

Reaction notes

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