Isopropyl isocyanate → HCID 69016299, compound

HRID 541628Notes

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]([CH:51]([CH3:53])[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][CH:51]([CH3:53])[CH3:52])=[O:50])[CH2:42][CH2:41]1

Participants

Reactant 2

HCID 61277Isopropyl isocyanate

HCID 86636141HCID 86636141, compound

Product 1

HCID 69016299HCID 69016299, compoundYield 41%

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 2-isocyanatopropane as starting materials in 41% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.43 (s, 1H), 9.33 (s, 1H), 9.31 (s, 1H), 8.12 (s, 1H), 7.98 (s, 1H), 7.73 (s, 1H), 7.21 (d, 1H), 7.04 (m, 2H), 6.87 (d, 1H), 6.78 (d, 1H), 6.09 (m, 1H), 3.95 (m, 2H), 3.72 (m, 1H), 2.83 (m, 4H), 2.62 (m, 2H), 2.27 (m, 2H), 1.91 (m, 1H), 1.62 (m, 2H), 1.12 (m, 2H), 1.00 (d, 6H). LCMS for C29H35ClN7O3 (M+H)+: m/z=548.2.

Sources & evidence

ORD record: ord-09b73e45439f4f69ac3e5b2c5255ea62
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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