Water → HCID 58654455, compound

HRID 1170540Notes

Reaction equation

HRID 1170540 reaction equation
FC(F)(F)C(O)=O.[N:8]1([C:13]2[N:18]=[C:17]([CH:19]3[CH:23]([C:24](=[O:27])[NH:25][CH3:26])[CH2:22][CH2:21][N:20]3[CH2:28][CH2:29][N:30]([CH2:38][C:39]3[CH:47]=[CH:46][C:42]4[O:43][CH2:44][O:45][C:41]=4[CH:40]=3)C(=O)OC(C)(C)C)[CH:16]=[C:15]([CH3:48])[N:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1.O.[OH-].[NH4+]>C(Cl)Cl>[N:8]1([C:13]2[N:18]=[C:17]([CH:19]3[CH:23]([C:24]([NH:25][CH3:26])=[O:27])[CH2:22][CH2:21][N:20]3[CH2:28][CH2:29][NH:30][CH2:38][C:39]3[CH:47]=[CH:46][C:42]4[O:43][CH2:44][O:45][C:41]=4[CH:40]=3)[CH:16]=[C:15]([CH3:48])[N:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 58654417HCID 58654417, compound

Product 1

HCID 58654455HCID 58654455, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (5.00 mL, 67.3 mmol) was added dropwise over 5 minutes to a 0° C. solution of tert-butyl 2-(2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-(methylcarbamoyl)pyrrolidin-1-yl)ethyl(benzo[d][1,3]dioxol-5-ylmethyl)carbamate (100 mg, 0.18 mmol) in CH2Cl2 (5 mL). The reaction mixture was warmed to rt over 30 minutes then water (20 mL) was added. The solution was brought to pH=9 with ammonium hydroxide (100 mL), extracted with CH2Cl2 (3×10 mL), the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford 50 mg (61%) of 2-(2-(1 H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-1-(2-(benzo[d][1,3]dioxol-5-ylmethylamino)ethyl)-N-methylpyrrolidine-3-carboxamide as yellow oil. [M−H]+ 462.00.

Workup

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4c28bee0a01148608f34e616ae6c241b
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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