Ethylamine → HCID 57687023, compound

HRID 908456Notes

Reaction equation

HRID 908456 reaction equation
[CH2:1]([NH2:3])[CH3:2].[NH2:4][C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=2)=[CH:7][C:6]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C(N(C(C)C)C(C)C)C>C1COCC1>[NH2:4][C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([S:17]([NH:3][CH2:1][CH3:2])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=2)=[CH:7][C:6]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 86630154HCID 86630154, compound

Product 1

HCID 57687023HCID 57687023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylamine (2M in methanol, 0.117 ml) was added in one portion to a solution of 3-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]benzenesulphonyl chloride (0.045 g) and N-ethyl-N-isopropylpropan-2-amine (0.030 ml) in THF (2 ml) at ambient temperature, and the resultant mixture stirred for 20 hours. The mixture was then evaporated to dryness in vacuo and redissolved in NMP (2 ml), filtered and purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 21 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and acetonitrile as eluents. Fractions containing the desired compound were evaporated to dryness to afford 3-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]-N-ethyl-benzenesulphonamide (0.007 mg); Mass Spectrum: M+H+ 395.13; RT 2.59 min.

Workup

  1. customThe mixture was then evaporated to dryness in vacuo
  2. dissolutionredissolved in NMP (2 ml)
  3. filtrationfiltered
  4. custompurified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 21 mm diameter, 100 mm length)
  5. additionFractions containing the desired compound
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-35b5cebdd5c144c4b7e09aa0cc6a8f70
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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