Phenyl isocyanate → HCID 69015062, compound

HRID 541618Notes

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][CH2:42][NH:41]1)=[O:39].[C:46]1([N:52]=[C:53]=[O:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=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: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][CH2:42][N:41]1[C:53]([NH:52][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:54])=[O:39]

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 86636146HCID 86636146, compound

Product 1

HCID 69015062HCID 69015062, compoundYield 44%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H using (2S)—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-2-carboxamide bis(trifluoroacetate) and phenyl isocyanate as starting materials in 44% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.43 (s, 2H), 9.36 (s, 1H), 8.30 (s, 1H), 8.11 (s, 1H), 7.98 (s, 1H), 7.72 (s, 1H), 7.58 (d, 2H), 7.25 (m, 3H), 7.04 (m, 2H), 6.95 (m, 1H), 6.85 (d, 1H), 4.53 (m, 1H), 3.68 (m, 1H), 3.50 (m, 1H), 2.85 (m, 4H), 2.20 (m, 1H), 2.01 (m, 3H). LCMS for C30H29ClN7O2 (M+H)+: m/z=554.2.

Sources & evidence

ORD record: ord-27dc5d8533364eb7a585a556497cfb87
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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