3-Isocyanatophenol → HCID 71227211, compound

HRID 2370006Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22]C(=O)CC3C4C(=CC=CC=4)N(C)C=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[N:36]([C:39]1[CH:40]=[C:41]([OH:45])[CH:42]=[CH:43][CH:44]=1)=[C:37]=[O:38]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:37]([NH:36][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([OH:45])[CH:40]=3)=[O:38])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 124834753-Isocyanatophenol

HCID 71226691N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide2×

Product 1

HCID 71227211HCID 71227211, compound

Procedure

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-(3-hydroxyphenyl)urea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (40 mg, 0.13 mmol) and 3-isocyanatophenol (40.4 mg, 0.15 mmol) according to General Procedure G to give 20 mg (34.4%) of white solid. Anal. Calcd. for C25H31N5O2 m/z 433.2, found: 434.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.31 (s, 1H), 8.66 (m, 1H), 8.52 (s, 1H), 8.41 (m, 1H), 7.41 (d, J=8.9 Hz, 2H), 6.97 (m, 4H), 6.66 (d, J=9.3 Hz, 2H), 6.34 (m, 2H), 3.79 (m, 1H), 3.56 (m, 3H), 3.26 (m, 2H), 3.00 (m, 1H), 2.11 (m, 2H), 1.92 (m, 1H), 1.78 (m, 1H), 1.62 (m, 1H), 1.49 (m, 1H), 1.32 (m, 6H).

Sources & evidence

ORD record: ord-e81a9cf2788c43a08ffb80822f7a1545
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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