1,2-Dichloro-3-isocyanatobenzene → HCID 67271728, compound

HRID 1696589Notes

Reaction equation

NC1N(C2C=C(CC(OCC)=O)C=CC=2)N=C(C2C=CSC=2)C=1.[NH2:24][C:25]1[N:29]([C:30]2[CH:31]=[C:32]([CH:36]([CH3:42])[C:37]([O:39]CC)=[O:38])[CH:33]=[CH:34][CH:35]=2)[N:28]=[C:27]([C:43]2[CH:47]=[CH:46][S:45][CH:44]=2)[CH:26]=1.[Cl:48][C:49]1[C:54]([Cl:55])=[CH:53][CH:52]=[CH:51][C:50]=1[N:56]=[C:57]=[O:58]>>[Cl:48][C:49]1[C:54]([Cl:55])=[CH:53][CH:52]=[CH:51][C:50]=1[NH:56][C:57](=[O:58])[NH:24][C:25]1[N:29]([C:30]2[CH:31]=[C:32]([CH:36]([CH3:42])[C:37]([OH:39])=[O:38])[CH:33]=[CH:34][CH:35]=2)[N:28]=[C:27]([C:43]2[CH:47]=[CH:46][S:45][CH:44]=2)[CH:26]=1

Participants

Reactant 3

HCID 330501,2-Dichloro-3-isocyanatobenzene

HCID 58851575HCID 58851575, compound

HCID 67272129HCID 67272129, compound

Product 1

HCID 67271728HCID 67271728, compound

Procedure

Using the same general approach as for Example 524, ethyl 2-(3-(5-amino-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)acetate (0.2258 g, 0.450 mmol, 1.00 eq) was transformed to ethyl 2-(3-(5-amino-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)propanoate. This, in turn, was combined with 2,3-dichlorophenyl isocyanate, according to general method A, to afford 2-(3-(5-(3-(2,3-dichlorophenyl)ureido)-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)propanoic acid. Using general method J, this product was combined with 0.5M NH3 in dioxane (4.50 ml, 2.25 mmol, 5.00 eq). to afford 0.1731 g (77%) of pure 1-(1-(3-(1-amino-1-oxopropan-2-yl)phenyl)-3-(thiophen-3-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea. 1H NMR (DMSO-d6): δ 9.38 (s, 1H), 8.82 (s, 1H), 8.12-8.09 (m, 1H), 7.88-7.87 (m, 1H), 7.62-7.60 (m, 1H), 7.57-7.42 (m, 6H), 7.36-7.31 (m, 2H), 6.89 (brs, 1H), 6.86 (s, 1H), 3.69 (q, 1H, J=7.2 Hz), 1.36 (d, 3H, J=7.2 Hz); MS (ESI) m/z: 500.0 (M+H+), 502.0 (M+2+H+).

Sources & evidence

ORD record: ord-ff96703f0f484abca23d654e349853bd
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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