Dimethylamine → HCID 66928123, compound

HRID 2065335Notes

Reaction equation

HRID 2065335 reaction equation
N#N.[C:3]([C:6]1[O:10][C:9]([CH2:11][N:12]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[N:21]=[CH:22][O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH2:32]O)[CH:26]=3)=[O:19])=[N:13]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].C[CH2:35][N:36](C(C)C)[CH:37](C)C.CS(Cl)(=O)=O.CNC.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1.CC(=O)OCC>[C:3]([C:6]1[O:10][C:9]([CH2:11][N:12]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[N:21]=[CH:22][O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH2:32][N:36]([CH3:37])[CH3:35])[CH:26]=3)=[O:19])=[N:13]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4]

Participants

10

Reactant 6

HCID 674DimethylamineHCID 947NitrogenHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66928957HCID 66928957, compound

Product 1

HCID 66928123HCID 66928123, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-[3-(2-hydroxy-ethyl)-phenyl]-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-3-yl]-amide (51 mg, 0.12 mmol) in CH2Cl2 (1.0 mL) was treated with DIPEA (0.03 mL, 0.18 mmol) followed by methanesulfonyl chloride (0.01 mL, 0.15 mmol). The reaction mixture was stirred at rt for 2.5 h before dimethylamine (0.9 mL of a 2N solution in THF, 1.8 mmol) was and the reaction mixture was further stirred at rt for 2 h. EA (10 mL) and sat. aq. NaHCO3 (10 mL) were added and the aqueous layer was extracted with EA (10 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by HPLC gave the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.76 min; [M+H]+=448.25.

Workup

  1. extractionthe aqueous layer was extracted with EA (10 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by HPLC

Sources & evidence

ORD record
ord-66b5f3e1928d4475aabeb965d9482d5f
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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