Cyclopentyl Isocyanate → HCID 69015579, compound

HRID 541613Notes

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:45]=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]([C@@H:40]1[CH2:44][CH2:43][NH:42][CH2:41]1)=[O:39].[N:46]([CH:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1)=[C:47]=[O:48]>>[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:45]=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]([C@@H:40]1[CH2:44][CH2:43][N:42]([C:47]([NH:46][CH:49]2[CH2:53][CH2:52][CH2:51][CH2:50]2)=[O:48])[CH2:41]1)=[O:39]

Participants

Reactant 2

HCID 643500Cyclopentyl Isocyanate

HCID 86636140HCID 86636140, compound

Product 1

HCID 69015579HCID 69015579, compoundYield 43%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H using (3R)—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]pyrrolidine-3-carboxamide bis(trifluoroacetate) and isocyanatocyclopentane as starting materials in 43% yield. LCMS for C29H33ClN7O2 (M+H)+: m/z=546.2.

Sources & evidence

ORD record: ord-3008b72fb99d4a7984cdeb6116f9fb3c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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