Pyrazinecarbonyl chloride → HCID 86636152, compound

HRID 541631Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:47]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38](=[O:46])[CH2:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[N:48]1[CH:53]=[CH:52][N:51]=[CH:50][C:49]=1[C:54](Cl)=[O:55]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:47]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38](=[O:46])[CH2:39][CH:40]1[CH2:45][CH2:44][N:43]([C:54]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][N:48]=2)=[O:55])[CH2:42][CH2:41]1

Participants

Reactant 2

HCID 88279Pyrazinecarbonyl chloride

HCID 86636141HCID 86636141, compound

Product 1

HCID 86636152HCID 86636152, compoundYield 36%

Procedure

The desired compound was prepared according to the procedure of Example A20, using N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20), 3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-2-piperidin-4-ylacetamide bis(trifluoroacetate) and pyrazine-2-carbonyl chloride as starting materials in 36% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.42 (s, 1H), 9.35 (s, 1H), 9.30 (s, 1H), 8.80 (s, 1H), 8.72 (s, 1H), 8.68 (s, 1H), 8.11 (s, 1H), 7.99 (s, 1H), 7.73 (s, 1H), 7.21 (d, 1H), 7.04 (m, 2H), 6.87 (d, 1H), 6.78 (d, 1H), 4.49 (m, 2H), 3.65 (m, 1H), 3.12 (m, 1H), 2.81 (m, 4H), 2.31 (m, 2H), 2.10 (m, 1H), 1.83 (m, 1H), 1.68 (m, 1H), 1.22 (m, 2H). LCMS for C30H30ClN8O2 (M+H)+: m/z=569.2.

Sources & evidence

ORD record: ord-12b77649e8064ff19a2b83364c649609
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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