Diisopropylethylamine → HCID 58337085, compound

HRID 1809177Notes

Reaction equation

HRID 1809177 reaction equation
CS([C:5]1[C:6]2[N:7]([C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][N:13]=2)[CH:8]=[CH:9][N:10]=1)(=O)=O.OC(C(F)(F)F)=O.[NH2:29][CH2:30][C:31]1[CH:32]=[C:33]([S:37]([NH2:40])(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[N:7]3[CH:8]=[CH:9][N:10]=[C:5]([NH:29][CH2:30][C:31]4[CH:32]=[C:33]([S:37]([NH2:40])(=[O:38])=[O:39])[CH:34]=[CH:35][CH:36]=4)[C:6]3=[N:13][CH:12]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 58337175HCID 58337175, compoundHCID 866550883-Aminomethyl-benzenesulfonamide TFA salt

Product 1

HCID 58337085HCID 58337085, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-Methanesulfonyl-3-(4-methoxy-phenyl)-imidazo[1,2-a]pyrazine (0.150 g, 0.495 mmol), 3-Aminomethyl-benzenesulfonamide TFA salt (0.223 g, 0.742 mmol), DIPEA (0.260 mL, 1.50 mmol) in NMP (0.66 mL) is stirred at 100° C. for 16 hours. The reaction mixture is diluted with AcOEt, washed with water and brine, dried with MgSO4 anh., filtered and evaporated. The crude is purified by column chromatography using a gradient of (Pet.Ether 40-60/AcOEt: 1/1 to 0/1) to give 3-{[3-(4-Methoxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide as a pale yellow solid (0.135 g, 67%). LC-MS m/z 410 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried with MgSO4 anh.
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude is purified by column chromatography

Sources & evidence

ORD record
ord-836998b3ca0f4979b0acadfc6bb94c63
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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