Triethylamine → HCID 49830711, compound

HRID 1710467Notes

Reaction equation

HRID 1710467 reaction equation
[CH:1]1([NH:4][CH2:5][C:6]2[CH:15]=[C:14]3[C:9]([NH:10][C:11](=[O:19])[C:12]4[N:13]3[CH:16]=[CH:17][CH:18]=4)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>O1CCOCC1>[CH:1]1([N:4]([CH2:5][C:6]2[CH:15]=[C:14]3[C:9]([NH:10][C:11](=[O:19])[C:12]4[N:13]3[CH:16]=[CH:17][CH:18]=4)=[CH:8][CH:7]=2)[S:28]([CH3:27])(=[O:30])=[O:29])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25156280HCID 25156280, compound

Product 1

HCID 49830711HCID 49830711, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of EXAMPLE 12 (26 mg) and triethylamine (25 μL) in 1 mL dioxane was added methanesulfonyl chloride (5.53 μL). The mixture was stirred for 24 hours and concentrated. The title compound was purified by RP-HPLC using a gradient elution of 10/90 to 70/30 acetonitrile/0.1% TFA in water at 254 nm over 30 minutes. The free base was isolated after eluting from an ion exchange column (10 g). 1H NMR (500 MHz, DMSO-d6) δ 11.28 (s, 1H), 8.14 (m, 1H), 7.95 (s, 1H), 7.29 (s, 2H), 7.03 (m, 1H), 6.70 (m, 1H), 4.41 (s, 2H), 2.96 (s, 3H), 2.46 (m, 1H), 0.68 (d, 4H).

Workup

  1. concentrationconcentrated
  2. customThe title compound was purified by RP-HPLC
  3. washa gradient elution of 10/90 to 70/30 acetonitrile/0.1% TFA in water at 254 nm over 30 minutes
  4. customThe free base was isolated
  5. washafter eluting from an ion exchange column (10 g)

Sources & evidence

ORD record
ord-803ee8dbc6a143f0b0c7c6b5d113e587
Source dataset
uspto-grants-2010_09
Patent number
US07790721B2

Reaction notes

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