Dimethylcarbamoyl Chloride → HCID 69019016, compound

HRID 541624Notes

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][N:49]([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]([N:49]([CH3:53])[CH3:48])=[O:51])[CH2:42][CH2:41]1

Participants

Reactant 2

HCID 6598Dimethylcarbamoyl Chloride

HCID 86636141HCID 86636141, compound

Product 1

HCID 69019016HCID 69019016, compoundYield 48%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H 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 N,N-dimethylcarbamoyl chloride as starting materials in 48% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.57 (s, 1H), 9.43 (s, 1H), 9.32 (s, 1H), 8.17 (s, 1H), 7.97 (s, 1H), 7.72 (s, 1H), 7.21 (d, 1H), 7.10 (m, 1H), 7.01 (d, 1H), 6.88 (d, 1H), 6.80 (d, 1H), 3.57 (d, 2H), 2.91 (m, 2H), 2.83 (m, 2H), 2.71 (m, 8H), 2.32 (d, 2H), 1.93 (m, 1H), 1.70 (m, 2H), 1.20 (m, 2H). LCMS for C28H33ClN7O2 (M+H)+: m/z=534.2.

Sources & evidence

ORD record: ord-fb5a15f621b24cbbbfc04ef4c5bcca80
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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