1,2-Dichloroethane → N-(3-chloro-phenyl)-2-(4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzylamino)-acetamide

HRID 410353Notes

Reaction equation

HRID 410353 reaction equation
Br.[F:2][C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:20][C:21]3[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=3)[C:12]2=[NH:29])=[CH:5][CH:4]=1.[NH2:32][CH2:33][C:34]([NH:36][C:37]1[CH:42]=[CH:41][C:40](Cl)=[CH:39][CH:38]=1)=[O:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].OS([O-])(=O)=O.[K+].[Cl:64]CCCl>>[Cl:64][C:39]1[CH:38]=[C:37]([NH:36][C:34](=[O:35])[CH2:33][NH:32][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([CH2:20][N:13]3[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:11]([CH2:10][CH2:9][CH2:8][O:7][C:6]4[CH:5]=[CH:4][C:3]([F:2])=[CH:31][CH:30]=4)[C:12]3=[NH:29])=[CH:22][CH:23]=2)[CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 516920Potassium bisulfateHCID 5049666Sodium triacetoxyborohydrideHCID 105836572-amino-N-(4-chlorophenyl)acetamideHCID 867624844-{3-[3-(4-Fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde hydrobromide salt

Product 1

HCID 46240774N-(3-chloro-phenyl)-2-(4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzylamino)-acetamideYield 17%

Procedure

A solution of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.25 g, 0.52 mmol), 2-amino-N-(4-chloro-phenyl)-acetamide (114 mg, 0.62 mmol) and sodium triacetoxyborohydride (0.183 g, 0.87 mmol) in 1,2-dichloroethane (25 ml) was stirred at 0° C. and then slowly warmed to rt where it was maintained for 16 h. After this time a saturated solution of KHSO4 was introduced and the suspension was filtered. The collected solid was washed with MeOH and H2O and then dried to provide N-(3-chloro-phenyl)-2-(4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzylamino)-acetamide (50 mg, 17%). HPLC-MS 572 [M+1]+, 287.

Workup

  1. temperaturewas maintained for 16 h
  2. filtrationthe suspension was filtered
  3. washThe collected solid was washed with MeOH and H2O
  4. customdried

Sources & evidence

ORD record
ord-e04be807383b4b2294bcfc22ceebca72
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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