Triethylamine → (S)-tert-butyl 2-((7-(4-(4-(cyclopropylsulfonyl)piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

HRID 57631

Reaction equation

HRID 57631 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([NH:23][CH2:24][C@@H:25]4[O:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:38]1([S:41](Cl)(=[O:43])=[O:42])[CH2:40][CH2:39]1.CCN(CC)CC>C(Cl)Cl>[CH:38]1([S:41]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:13]4[N:22]=[C:21]([NH:23][CH2:24][C@@H:25]5[O:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]5)[C:20]5[C:15](=[N:16][CH:17]=[CH:18][N:19]=5)[CH:14]=4)=[CH:11][CH:12]=3)[CH2:2][CH2:3]2)(=[O:43])=[O:42])[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 86717391(S)-tert-butyl 2-((7-(4-(piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Product 1

HCID 86717393(S)-tert-butyl 2-((7-(4-(4-(cyclopropylsulfonyl)piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylateYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-tert-butyl 2-((7-(4-(piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (100 mg, 0.20 mmol), cyclopropanesulfonyl chloride (33 mg, 0.24 mmol) and Et3N (41 mg, 0.40 mmol) in 5 mL of DCM at 0° C. was stirred at room temperature for 1 hour. The volatiles were removed in vacuo, and the residues was purified by chromatography with PE/EA (1:2˜1:10) to give 52 mg of title compound.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residues was purified by chromatography with PE/EA (1:2˜1:10)

Sources & evidence

ORD record
ord-7a707564977b42a09ab523be24f057d4
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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