Diisopropylethylamine → HCID 11361581, compound

HRID 2242911Notes

Reaction equation

HRID 2242911 reaction equation
[NH2:1][CH2:2][C:3]#[C:4][C:5]1[N:6]=[C:7]([NH2:19])[C:8]2[N:9]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:10]=1.[S:20]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21]1.CCN(C(C)C)C(C)C>C1COCC1.CN(C1C=CN=CC=1)C.O>[NH2:19][C:7]1[C:8]2[N:9]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:10]=[C:5]([C:4]#[C:3][CH2:2][NH:1][S:25]([C:22]2[CH:23]=[CH:24][S:20][CH:21]=2)(=[O:27])=[O:26])[N:6]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 2776378Thiophene-3-sulfonyl ChlorideHCID 11817648HCID 11817648, compound

Product 1

HCID 11361581HCID 11361581, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3-amino-prop-1-ynyl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (0.1 mmol, see Example 26 below) in THF (1 mL) was added thiophene-3-sulfonyl chloride (23.7 mg, 0.13 mmol), a catalytic quantity of DMAP and Hünig's base (52 uL, 0.3 mmol) successively. The reaction was stirred overnight and diluted with water. The aqueous layer was extracted with methylene chloride. The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was then evaporated. The residue was purified using preparative HPLC (C18, H2O:MeCN gradient) to afford the desired product. 1H NMR (400 MHz, DMSO-d6) δ8.16 (1H), 8.09 (1H), 7.86 (1H), 7.68 (1H), 7.54 (1H), 7.31 (1H), 7.07(1H), 6.65 (1H), 4.23 (2H), 3.53 (d, J=7 Hz, 2H). MS: m/z 401 [M+1].

Workup

  1. extractionThe aqueous layer was extracted with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was then evaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-e1c80ef601344a04853e3cce4bc97758
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

Loading…