Phenyl isocyanate → HCID 71226633, compound

HRID 2369982Notes

Reaction equation

[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:10]([C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([NH:25][C@@H:26]3[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]3[NH2:32])[CH2:20]2)=[N:17][CH:18]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([NH:25][C@@H:26]3[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]3[NH:32][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[CH2:20]2)=[N:17][CH:18]=1)([O-:12])=[O:11]

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 71226921HCID 71226921, compound

Product 1

HCID 71226633HCID 71226633, compoundYield 51.7%

Procedure

1-((1R,2R)-2-((S)-1-(5-Nitropyrimidin-2-yl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea (17.5 mg, 0.031 mmol, 51.5% yield) was synthesized as described in General Procedure F using phenyl isocyanate (7.15 mg, 0.060 mmol) and (1R,2R)—N1-((S)-1-(5-nitropyrimidin-2-yl)piperidin-3-yl)cyclohexane-1,2-diamine (32.9 mg, 0.060 mmol). Anal. Calcd. for C22H29N7O3 m/z 439.5, found: 440.4 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 10.25 (br. s., 1H), 8.90 (d, J=6.60 Hz, 1H), 8.78-8.59 (m, 2H), 7.23-7.123 (m, 4H), 6.98 (t, J=6.87 Hz, 1H), 6.56 (br. s., 1H), 4.27 (d, J=12.09 Hz, 1H), 4.12-3.92 (m, 2H), 3.88-3.73 (m, 1H), 3.64 (br. s., 1H), 3.21 (br. s., 1H), 3.02-2.77 (m, 3H), 2.20-2.00 (m, 2H), 1.92 (ddd, J=7.01, 3.44, 3.30 Hz, 1H), 1.80 (d, J=10.99 Hz, 2H), 1.63 (d, J=14.29 Hz, 3H), 1.35-1.11 (m, 2H).

Sources & evidence

ORD record: ord-f19dfdad9d474390967bd35d86245ccf
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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