Phenyl isocyanate → HCID 69016001, compound

HRID 541615Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[NH2:15][CH2:16][C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]2[NH:24][C:25]3[N:41]=[C:29]([NH:30][C:31]4[CH:32]=[CH:33][CH:34]=[C:35]([CH:40]=4)[CH2:36][CH2:37][C:38]=1[CH:39]=2)[N:28]=[CH:27][C:26]=3[Cl:42])=[O:18].[C:43]1([N:49]=[C:50]=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:49]([C:50]([NH:15][CH2:16][C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]2[NH:24][C:25]3[N:41]=[C:29]([NH:30][C:31]4[CH:32]=[CH:33][CH:34]=[C:35]([CH:40]=4)[CH2:36][CH2:37][C:38]=1[CH:39]=2)[N:28]=[CH:27][C:26]=3[Cl:42])=[O:18])=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 86636143HCID 86636143, compound

Product 1

HCID 69016001HCID 69016001, compoundYield 38%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H using 2-amino-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]acetamide bis(trifluoroacetate) and phenyl isocyanate as starting materials in 38% yield. LCMS for C27H25ClN7O2 (M+H)+: m/z=514.2.

Sources & evidence

ORD record: ord-72bc53d493b6421cb11c505e98944b66
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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