1-Isocyanato-2-phenylbenzene → HCID 66616621, compound

HRID 1889684Notes

Reaction equation

HRID 1889684 reaction equation
[Cl:1][C:2]1[C:3]([OH:40])=[C:4]([S:9]([N:12]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:41]1[CH:46]=[CH:45][C:44]([C:47]2[C:52]([N:53]=[C:54]=[O:55])=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:43][CH:42]=1>C1COCC1>[C:47]1([C:44]2[CH:45]=[CH:46][CH:41]=[CH:42][CH:43]=2)[CH:48]=[CH:49][CH:50]=[CH:51][C:52]=1[NH:53][C:54](=[O:55])[N:21]([CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:12]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)=[CH:29][CH:28]=1)[S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:40])(=[O:11])=[O:10])[CH2:22][CH:23]([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 2222801-Isocyanato-2-phenylbenzeneHCID 585313773,5-Dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxy-N-(3-((isobutyl amino)methyl)benzyl)benzene sulfonamide2×

Product 1

HCID 66616621HCID 66616621, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dichloro-N-((4′-fluorobiphenyl-4-yl)methyl)-2-hydroxy-N-(3-((isobutyl amino)methyl)benzyl)benzene sulfonamide (Compound E of Example 184, 0.04 g, 0.0667 mmol, 1.0 eq) in a 5 mL of THF at 0° C. was added 2-biphenyl isocyanate (0.013 g, 0.0667 mmol, 1.0 eq). The reaction mixture was stirred at ambient temperature for 15 min and concentrated to remove the volatiles. The residue was purified by preparative HPLC to afford the title compound (0.03 g, 60%). 1H NMR (400 MHz, DMSO-d6) δ 0.66-0.68 (d, 6H), 1.7 (m, 1H), 2.82-2.84 (d, 2H), 4.30 (s, 2H), 4.43 (d, 4H), 6.84-6.89 (t, 2H), 6.99 (d, 1H), 7.14-7.20 (m, 4H), 7.23 (m, 4H), 7.25-7.34 (m, 5H), 7.44-7.46 (d, 3H), 7.57-7.62 (m, 4H), 7.80 (s, 1H). MS (HD: 796.1 (M−H)−.

Workup

  1. concentrationconcentrated
  2. customto remove the volatiles
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-24c3c44e96364961a127ae233d04d79d
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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