Isopropyl chloroformate → HCID 59310748, compound

HRID 2240667Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[S:38](=[O:40])(=[O:39])[NH:37][C:36](=[O:41])[CH2:35]5)=[CH:30][CH:29]=4)[CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])[N:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:43][C:44]1[CH:48]=[C:47]([CH3:49])[O:46][N:45]=1.Cl[C:51]([O:53][CH:54]([CH3:56])[CH3:55])=[O:52]>>[CH:54]([O:53][C:51](=[O:52])[N:1]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH2:35][C:36](=[O:41])[NH:37][S:38]5(=[O:40])=[O:39])=[CH:30][CH:29]=4)[CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])[N:19]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:43][C:44]1[CH:48]=[C:47]([CH3:49])[O:46][N:45]=1)([CH3:56])[CH3:55]

Participants

Reactant 3

HCID 7917Isopropyl chloroformate

HCID 27763043-(Bromomethyl)-5-methylisoxazole

HCID 68582869HCID 68582869, compound

Product 1

HCID 59310748HCID 59310748, compound

Procedure

5-{4-[2-(4′-Amino-biphenyl-4-ylmethyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide (61 mg, 0.1 mmol) was treated subsequently according to general procedure K using 3-(bromomethyl)-5-methylisoxazole (27 mg, 0.15 mmol) and general procedure U using isopropyl chloroformate (1M solution in toluene) (0.2 mL, 0.2 mmol) to give (4′-{4-(2,4-dichloro-phenyl)-1-[4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-phenyl]-1H-imidazol-2-ylmethyl}-biphenyl-4-yl)-(5-methyl-isoxazol-3-ylmethyl)-carbamic acid isopropyl ester.

Sources & evidence

ORD record: ord-aec23943e53b4be5bc96d242e8a08601
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723369B2

Reaction notes

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