Water → HCID 90412318, compound

HRID 1522033Notes

Reaction equation

HRID 1522033 reaction equation
[F:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH:13]4[CH2:17][NH:16][CH2:15][CH:14]4[CH:18]=3)[NH:8][C:5]2=[N:6][CH:7]=1.Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].C(N(CC)CC)C.O>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH:13]4[CH2:17][N:16]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:15][CH:14]4[CH:18]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 90413493HCID 90413493, compound

Product 1

HCID 90412318HCID 90412318, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 282A (400 mg, 0.908 mmol), tert-butyl 2-bromoacetate (0.157 mL, 1.090 mmol), and triethylamine (0.633 mL, 4.54 mmol) in N,N-dimethylformamide (7 mL) was heated at 85° C. for 30 minutes in a Biotage Initiator microwave reactor. The mixture was treated with water and brine and extracted with ethyl acetate (twice). The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using the ISCO Companion eluting with ethyl acetate/heptanes (7:3 to 8:2) to give the title compound. MS (ESI+) m/z 481.9 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (twice)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel using the ISCO Companion
  7. washeluting with ethyl acetate/heptanes (7:3 to 8:2)

Sources & evidence

ORD record
ord-ac20273db3544664ac72afa215fcc25c
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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