Triethylamine → Tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate

HRID 1504892Notes

Reaction equation

HRID 1504892 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[S:27]([CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:29])=[O:28]>C(Cl)Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][S:27]([CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])(=[O:29])=[O:28])=[CH:3][C:4]=1[NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=1)#[N:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 17750969tert-butyl N-[2-(chlorosulfonyl)ethyl]carbamate2×HCID 867316535-Amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

Product 1

HCID 131734337Tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (PrepEx 1.8) (150 mg, 0.63 mmol) in DCM (5 mL) was added triethylamine (0.26 mL, 1.88 mmol) followed by the dropwise addition of tert-butyl [2-(chlorosulfonyl)ethyl]carbamate (25% w/w in DCM, 920 mg, 0.94 mmol). The reaction mixture was stirred for 3 hours at room temperature. Additional tert-butyl [2-(chlorosulfonyl)ethyl]carbamate (25% w/w in DCM, 920 mg, 0.94 mmol) was added and the reaction mixture was stirred for 16 hours. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organics were separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford tert-butyl [2-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}sulfamoyl)ethyl]carbamate. MS ESI calc'd. for C20H27N6O4S [M+H]+ 447. found 447. 1H NMR (500 MHz, DMSO-d6) δ 10.70 (s, 1H), 9.19 (s, 1H), 8.50 (s, 1H), 8.01 (s, 1H), 6.86 (t, J=5.5 Hz, 1H), 6.73 (s, 1H), 6.65 (s, 1H), 3.41 (t, J=6.7 Hz, 2H), 3.32-3.29 (m, 2H), 2.31 (s, 3H), 2.22 (s, 3H), 1.30 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred for 16 hours
  2. customThe organics were separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a25410cd57f94c038dcd66a99bf96f80
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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