Hydroxyamine hydrochloride → HCID 117777556, compound

HRID 64191Notes

Reaction equation

HRID 64191 reaction equation
[C:1]([C:4]1[CH:33]=[CH:32][C:7]2[N:8]([C:11]3[CH:12]=[C:13]([NH:25][S:26]([CH:29]4[CH2:31][CH2:30]4)(=[O:28])=[O:27])[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[F:24])[CH:16]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[OH:35][NH2:36]>C(O)C>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:15]1[CH:16]=[C:11]([N:8]2[C:7]3[CH:32]=[CH:33][C:4](/[C:1](=[N:36]\[OH:35])/[CH3:2])=[CH:5][C:6]=3[N:10]=[CH:9]2)[CH:12]=[C:13]([NH:25][S:26]([CH:29]2[CH2:31][CH2:30]2)(=[O:27])=[O:28])[CH:14]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 89501309N-(5-(5-acetyl-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamide

Product 1

HCID 117777556HCID 117777556, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(5-(5-acetyl-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide (110 mg, 0.235 mmol) in ethanol was added hydroxyl amine hydrochloride (24.7 mg, 0.353 mmol) and the mixture was heated at 80° C. for 2 h. The mixture was concentrated under vacuum and washed with ether to afford the product in 49% yield (55 mg). 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1H), 8.03 (s, 1H), 7.82-7.70 (m, 3H), 7.60-7.58 (d, 2H), 7.52 (s, 1H), 7.46-7.40 (m, 1H), 7.27-7.24 (m, 1H), 2.86-2.83 (m, 1H), 2.25 (s, 3H), 1.01-1.00 (m, 4H); LC-MS (ESI): Calculated mass: 482.5; Observed mass: 483.1 [M+H]+ (rt: 1.475 min).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. washwashed with ether
  3. customto afford the product in 49% yield (55 mg)
  4. custom483.1 [M+H]+ (rt: 1.475 min)

Sources & evidence

ORD record
ord-57d8ba5f80d347bd8cf23efa6e4ff15d
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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