Phenyl isocyanate → HCID 69013371, compound

HRID 541608Notes

Reaction equation

HRID 541608 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.[C:48]1([N:54]=[C:55]=[O:56])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[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:55]([NH:54][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:56])[CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 86636141HCID 86636141, compound

Product 1

HCID 69013371HCID 69013371, compoundYield 53%

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 phenyl isocyanate as starting materials in 53% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.49 (s, 1H), 9.38 (s, 1H), 9.35 (s, 1H), 8.47 (s, 1H), 8.12 (s, 1H), 7.99 (s, 1H), 7.72 (s, 1H), 7.43 (d, 2H), 7.20 (m, 3H), 7.04 (m, 2H), 6.90 (m, 2H), 6.78 (d, 1H), 4.15 (d, 2H), 2.82 (m, 6H), 2.30 (d, 2H), 2.00 (m, 1H), 1.72 (m, 2H), 1.20 (m, 2H). LCMS for C32H33ClN7O2 (M+H)+: m/z=582.2.

Sources & evidence

ORD record
ord-c2817a3eaa8a4a82aae73cd391b3ca80
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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