Triethylamine → HCID 67002189, compound

HRID 2191571Notes

Reaction equation

HRID 2191571 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH:20]4[CH2:22][CH2:21]4)[N:18]=3)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:12]=2)=[O:10])[CH2:3]1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:38][S:39]([N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH:20]4[CH2:22][CH2:21]4)[N:18]=3)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:12]=2)=[O:10])[CH2:3]1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67002083HCID 67002083, compound

Product 1

HCID 67002189HCID 67002189, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 15 mL round-bottomed flask, 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid piperidin-3-ylamide hydrochloride (200 mg, 0.44 mmol) was dissolved in CH2Cl2 (3 mL) and cooled to 0° C. Added triethylamine (0.12 mL, 0.88 mmol) followed by methanesulfonyl chloride (0.04 mL, 0.48 mmol). The reaction mixture was stirred at room temperature for 6 h then diluted with 30 mL of CH2Cl2 and washed with water (5 mL). The aqueous layer was extracted with CH2Cl2 (30 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography over 12 g SiO2 with EtOAc/Hexanes (gradient: 0-100% EtOAc) to provide 174 mg (89%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-piperidin-3-yl)-amide as a white foam.

Workup

  1. washwashed with water (5 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (30 mL)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography over 12 g SiO2 with EtOAc/Hexanes (gradient: 0-100% EtOAc)

Sources & evidence

ORD record
ord-e6f8a4d862054895b5ab2c378f006c46
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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