Ethyl isocyanate → HCID 69018805, compound

HRID 541607Notes

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.[N:48]([CH2:51][CH3:52])=[C:49]=[O:50]>>[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:49]([NH:48][CH2:51][CH3:52])=[O:50])[CH2:42][CH2:41]1

Participants

Reactant 2

HCID 8022Ethyl isocyanate

HCID 86636141HCID 86636141, compound

Product 1

HCID 69018805HCID 69018805, compoundYield 77%

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 isocyanato-ethane as starting materials in 77% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.65 (s, 1H), 9.60 (s, 1H), 9.30 (s, 1H), 8.20 (s, 1H), 7.92 (s, 1H), 7.73 (s, 1H), 7.24 (d, 1H), 7.12 (m, 1H), 7.04 (d, 1H), 6.87 (d, 1H), 6.80 (d, 1H), 6.40 (s, 1H), 3.92 (d, 2H), 3.01 (m, 2H), 2.90 (m, 4H), 2.62 (m, 2H), 2.28 (d, 2H), 1.92 (m, 1H), 1.61 (m, 2H), 1.12 (m, 2H), 1.00 (t, 3H). LCMS for C28H33ClN7O2 (M+H)+: m/z=534.2.

Sources & evidence

ORD record: ord-66581682c7e548b0b571c19c72663a0f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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