Ammonium Chloride → HCID 178481998, compound

HRID 1960009Notes

Reaction equation

HRID 1960009 reaction equation
[F:1][C:2]([F:50])([F:49])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:27]2[CH2:31][CH2:30][CH2:29][C@@H:28]2[C@H:32]2[CH2:37][CH2:36][C@H:35]([CH2:38][C:39](O)=[O:40])[CH2:34][CH2:33]2)=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([F:25])=[C:20]([F:26])[CH:19]=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[NH4+].[Cl-].Cl.C([N:56]=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O.C(N(CC)CC)C>[F:48][C:45]([F:47])([F:46])[C:43]1[CH:42]=[C:5]([CH:4]=[C:3]([C:2]([F:50])([F:49])[F:1])[CH:44]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:27]2[CH2:31][CH2:30][CH2:29][C@@H:28]2[C@H:32]2[CH2:37][CH2:36][C@H:35]([CH2:38][C:39]([NH2:56])=[O:40])[CH2:34][CH2:33]2)=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([F:25])=[C:20]([F:26])[CH:19]=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482001HCID 178482001, compound

Product 1

HCID 178481998HCID 178481998, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-(4-{(R)-1-[3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexyl)acetic acid (85 mg, 0.12 mmol) in DMF (3 mL) is added NH4Cl (10 mg, 0.18 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl 41 mg, 0.18 mmol), 1-hydroxy-7-azabenzotriazole (HOAt, 24 mg, 0.18 mmol), and small amount of triethylamine. After stirring for 2 hours at room temperature, the reaction mixture is diluted with EtOAc, washed successively with water and brine, and dried over magnesium sulfate. Evaporation of the solvent and purification by silica gel column using ethyl acetate-hexane affords trans-(4-{(R)-1-[3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexyl)acetic acid amide.

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent and purification by silica gel column

Sources & evidence

ORD record
ord-1e38cb84b153446595d9fe190e0fe55d
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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