Pivaloyl chloride → HCID 69014469, compound

HRID 541632Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[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.[CH3:48][C:49]([CH3:54])([CH3:53])[C:50](Cl)=[O:51]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[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:50](=[O:51])[C:49]([CH3:54])([CH3:53])[CH3:48])[CH2:42][CH2:41]1

Participants

Reactant 2

HCID 62493Pivaloyl chloride

HCID 86636141HCID 86636141, compound

Product 1

HCID 69014469HCID 69014469, compoundYield 31%

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 2,2-dimethylpropanoyl chloride as starting materials in 31% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.50 (s, 1H), 9.33 (s, 1H), 9.30 (s, 1H), 8.13 (s, 1H), 7.98 (s, 1H), 7.77 (s, 1H), 7.21 (d, 1H), 7.04 (m, 2H), 6.87 (d, 1H), 6.79 (d, 1H), 4.27 (m, 2H), 2.81 (m, 6H), 2.25 (m, 2H), 2.01 (m, 1H), 1.76 (m, 2H), 1.19 (s, 9H), 1.04 (m, 2H). LCMS for C30H36ClN6O2 (M+H)+: m/z=547.2.

Sources & evidence

ORD record: ord-01acf1e7c33141de98007cca789a94fe
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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