Dimethylformamide → HCID 23582356, compound

HRID 1865856Notes

Reaction equation

HRID 1865856 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:25])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].C[N:32]([CH:34]=O)C>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:25])[NH:17][C:18]1[CH:19]=[C:20]([C:2]2[CH:7]=[CH:6][C:34]([NH2:32])=[CH:4][CH:3]=2)[CH:21]=[CH:22][CH:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 23582882HCID 23582882, compound

Product 1

HCID 23582356HCID 23582356, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (S)-2-(3-Bromo-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (201 mg, 0.5 mmol), 6-4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1 eq., 108 mg), Pd[P(Ph)3]4 (5 mol %, 20 mg), in methanol (6 mL), NaHCO3 (sat. aq., 900 uL) and DMF (1.5 mL) was degassed and heated to 70° C. overnight in a sealed vial. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the products. Yield 26 mg. MS: 440.3 (M+H). H1-NMR (DMSO-d6): δ (ppm) 10.1 (s, 1H), 7.9 (m, 1H), 7.5-7.0 (m, 12H), 5.0 (m, 2H), 4.4 (m, 1H), 3.5 (m, 1H), 2.2 (m, 1H), 1.9 (m, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customthe solvents removed
  4. dissolutionThe resulting mixture was redissolved in 5 ml of 90% DMF
  5. custom10% water with 0.1% TFA and purified by reverse phase HPLC
  6. customto give the products

Sources & evidence

ORD record
ord-3b1d8d7bb06c4216b5921f060497ee84
Source dataset
uspto-grants-2009_12
Patent number
US07629340B2

Reaction notes

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