4-(Trifluoromethyl)phenyl isocyanate → HCID 178522059, compound

HRID 572243Notes

Reaction equation

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

Participants

Reactant 3

HCID 737684-(Trifluoromethyl)phenyl isocyanate

HCID 178511704HCID 178511704, compound

HCID 178522077HCID 178522077, compound

Product 1

HCID 178522059HCID 178522059, compoundYield 70%

Procedure

Compound 2372 was prepared in 70% yield from 4-(trifluoromethyl)phenyl isocyanate and trans-4-(4-amino-cyclohexyloxy)-benzoic acid using the procedure detailed for compound 2221 in Example 4. 1H NMR (400 MHz, DMSO-d6): δ 12.62 (s, 1H), 9.00 (s, 1H), 7.86 (d, J=9 Hz, 2H), 7.60-7.53 (m, 4H), 7.02 (d, J=9 Hz, 2H), 6.52 (d, J=8 Hz, 1H), 4.50-4.40 (m, 1H), 3.60-3.48 (m, 1H), 2.11-2.01 (m, 2H), 1.98-1.89 (m, 2H), 1.56-1.32 (m, 4H).

Sources & evidence

ORD record: ord-55db0c5bd78545f3b1864feaf7e7ae0f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029401B2

Reaction notes

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