1,2-Dichloro-3-isocyanatobenzene → HCID 67270552, compound

HRID 1696590Notes

Reaction equation

HRID 1696590 reaction equation
NC1N(C2C=C(CC(OCC)=O)C=CC=2)N=C(C2SC=CC=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[S:44][CH:45]=[CH:46][CH:47]=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[S:44][CH:45]=[CH:46][CH:47]=2)[CH:26]=1

Participants

4

Reactant 3

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 58851486HCID 58851486, compoundHCID 67271903HCID 67271903, compound

Product 1

HCID 67270552HCID 67270552, compound

Procedure

Using the same general approach as for Example 524, ethyl 2-(3-(5-amino-3-(thiophen-2-yl)-1H-pyrazol-1-yl)phenyl)acetate (0.202 g, 0.403 mmol, 1.00 eq) was transformed to ethyl 2-(3-(5-amino-3-(thiophen-2-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-2-yl)-1H-pyrazol-1-yl)phenyl)propanoic acid. Using general method J, this product was combined with 0.5M NH3 in dioxane (4.03 ml, 2.01 mmol, 5.00 eq) to afford 0.145 g (72%) of 1-(1-(3-(1-amino-1-oxopropan-2-yl)phenyl)-3-(thiophen-2-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea.

Sources & evidence

ORD record
ord-138b66cbfa394576a7fcff247cf28fc1
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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