1,2-Dichloro-3-isocyanatobenzene → HCID 67271075, compound

HRID 1696511Notes

Reaction equation

HRID 1696511 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:11]=[CH:10]3)[N:5]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=1.[Cl:27][C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=1[N:35]=[C:36]=[O:37]>>[C:23]([C:4]1[CH:3]=[C:2]([NH:1][C:36]([NH:35][C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([Cl:34])[C:28]=2[Cl:27])=[O:37])[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[N:11]=[CH:10]3)[N:5]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 67253077HCID 67253077, compound

Product 1

HCID 67271075HCID 67271075, compoundYield 50.4%

Procedure

Using general method A, t-butyl 5-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (0.150 g, 0.422 mmol, 1.00 eq) and 2,3-dichlorophenyl isocyanate (0.0557 ml, 0.422 mmol, 1.00 eq). were combined to yield t-butyl 5-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (115.5 mg, 50% yield). 1H NMR (DMSO-d6): δ 9.25 (s, 1H), 8.73 (s, 1H), 8.53 (brs, 1H), 8.22-8.19 (m, 1H), 8.06-8.01 (m, 2H), 7.79-7.76 (m, 1H), 7.33-7.29 (m, 2H), 6.43 (s, 1H), 1.67 (s, 9H), 1.30 (s, 9H); MS (ESI) m/z: 543.0 (M+H+), 545.0 (M+2+H+).

Sources & evidence

ORD record
ord-aa171a1a105b4bf7ab4337fbcc2ac267
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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