1-Isocyanatoadamantane → HCID 68281294, compound

HRID 572240Notes

Reaction equation

[C:1]12([N:11]=[C:12]=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:14][NH:15][C:16]([C:18]1[CH:23]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH:21]=[CH:20][N:19]=1)=[O:17].ClC1C=CC(NC(=O)N[C@H]2CC[C@H](OC3C=CC(C(O)=O)=CC=3)CC2)=CC=1C(F)(F)F>>[CH3:14][NH:15][C:16]([C:18]1[CH:23]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:12]([NH:11][C:1]34[CH2:10][CH:5]5[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]5)[CH2:2]3)[CH2:8]4)=[O:13])=[CH:27][CH:26]=2)[CH:21]=[CH:20][N:19]=1)=[O:17]

Participants

Reactant 3

HCID 20599951-Isocyanatoadamantane

HCID 166551294-(4-Aminophenoxy)-N-methylpicolinamide

HCID 178522077HCID 178522077, compound

Product 1

HCID 68281294HCID 68281294, compoundYield 60%

Procedure

Compound 2287 was prepared in 60% yield from adamantyl isocyanate and 4-(4-amino-phenoxy)-pyridine-2-carboxylic acid methylamide using the procedure detailed for compound 2221 in Example 4. 1H NMR (300 MHz, DMSO-d6) δ 8.73 (q, J=5 Hz, 1H), 8.48 (d, J=6 Hz, 1H), 8.39 (s, 1H), 7.49-7.42 (m, 2H), 7.36 (d, J=2 Hz, 1H), 7.13-7.03 (m, 3H), 5.89 (s, 1H), 2.78 (d, J=5 Hz, 3H), 2.09-2.01 (m, 3H), 1.98-1.92 (m, 6H), 1.68-1.60 (m, 61).

Sources & evidence

ORD record: ord-b6bab67ed2ec4d19b738ca7ab43ac6bc
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029401B2

Reaction notes

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