Dichloromethane → 4-[5-(2-Amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzonitrile dihydrochloride

HRID 1594862Notes

Reaction equation

HRID 1594862 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[N:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]4([CH2:41][CH3:42])[CH2:38][CH2:37][CH2:36][CH2:35][N:34]([CH3:39])[C:33]4=[O:40])[CH:27]=3)[CH:18]=2)[C:12]([CH3:15])=[N:13][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:52]>>[ClH:52].[ClH:52].[NH2:7][CH2:8][CH2:9][C:10]1[N:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]4([CH2:41][CH3:42])[CH2:38][CH2:37][CH2:36][CH2:35][N:34]([CH3:39])[C:33]4=[O:40])[CH:27]=3)[CH:18]=2)[C:12]([CH3:15])=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 54508564[2-(3-{4-cyano-3-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzyl}-2-methyl-3H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 217062014-[5-(2-Amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzonitrile dihydrochloride

Procedure

To a solution of [2-(3-{4-cyano-3-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzyl}-2-methyl-3H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (as described in Step B above) (0.2 g, 0.41 mmol) in CH2Cl2 (6.0 mL) was added TFA (3.0 mL) and the solution was stirred for 0.5 hr. The solvents were removed in vacuo and the crude product was purified by preparative HPLC. Conversion to the HCl salt yielded the title compound.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c747706e699b4895b0ac98161f3d528b
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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