Pyrazinecarbonyl chloride → HCID 86636166, compound

HRID 541646Notes

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].[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:54]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH:44][C:45](=[O:53])[CH2:46][CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.[N:55]1[CH:60]=[CH:59][N:58]=[CH:57][C:56]=1[C:61](Cl)=[O:62]>>[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].[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:54]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH:44][C:45](=[O:53])[CH2:46][CH:47]1[CH2:52][CH2:51][N:50]([C:61]([C:56]2[CH:57]=[N:58][CH:59]=[CH:60][N:55]=2)=[O:62])[CH2:49][CH2:48]1

Participants

Reactant 2

HCID 88279Pyrazinecarbonyl chloride

HCID 86636131N-[6-chloro-2,4,8,18,22-pentaazatetracyclo[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 tris(trifluoroacetate)

Product 1

HCID 86636166HCID 86636166, compoundYield 46%

Procedure

The desired compound was prepared according to the procedure of Example A20, using N-[6-chloro-2,4,8,18,22-pentaazatetracyclo[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 tris(trifluoroacetate) and pyrazine-2-carbonyl chloride as starting materials in 46% yield. 1H NMR (300 MHz, DMSO-d6): δ 10.10 (s, 1H), 9.40 (m, 2H), 9.05 (s, 1H), 8.80 (s, 1H), 8.71 (s, 1H), 8.67 (s, 1H), 8.32 (d, 2H), 8.20 (s, 1H), 7.65 (s, 1H), 7.30 (d, 1H), 7.04 (d, 1H), 4.52 (d, 1H), 3.62 (d, 1H), 3.12 (m, 1H), 2.98 (m, 4H), 2.88 (m, 1H), 2.34 (m, 2H), 2.12 (m, 1H), 1.82 (m, 1H), 1.70 (m, 1H), 1.25 (m, 2H). LCMS for C29H29ClN9O2 (M+H)+: m/z=570.2.

Sources & evidence

ORD record: ord-509170d3617843899942542e8c01cfc5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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