Formaldehyde → (S)-7-(4-(4-methyl piperazin-1-yl)phenyl)-N-((4-(methylsulfonyl)morpholin-2-yl)methyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57653Notes

Reaction equation

HRID 57653 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][O:8][C@@H:7]([CH2:11][NH:12][C:13]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][N:21]=3)[CH:16]=[C:15]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[N:14]=2)[CH2:6]1)(=[O:4])=[O:3].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:39](C)=O.[Na+]>C(Cl)Cl>[CH3:39][N:32]1[CH2:31][CH2:30][N:29]([C:26]2[CH:27]=[CH:28][C:23]([C:15]3[N:14]=[C:13]([NH:12][CH2:11][C@@H:7]4[O:8][CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:6]4)[C:22]4[C:17](=[N:18][CH:19]=[CH:20][N:21]=4)[CH:16]=3)=[CH:24][CH:25]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86717411(S)-N-((4-(methylsulfonyl)morpholin-2-yl)methyl)-7-(4-(piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-amine

Product 1

HCID 86717410(S)-7-(4-(4-methyl piperazin-1-yl)phenyl)-N-((4-(methylsulfonyl)morpholin-2-yl)methyl)pyrido[4,3-b]pyrazin-5-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)—N-((4-(methylsulfonyl)morpholin-2-yl)methyl)-7-(4-(piperazin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-amine (60 mg, 0.12 mmol), Formalin (48 mg, 0.48 mmol) and NaBH(AcO)3 in 5 mL of DCM, was stirred at room temperature for 2 hours. The volatiles were removed in vacuo, and the residue was purified by chromatography with MeOH/H2O (1:10˜10:1) to give 46 mg of title compound. MS (m/z)=498 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by chromatography with MeOH/H2O (1:10˜10:1)

Sources & evidence

ORD record
ord-aef304d8b646426b8ee363dc47096343
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

Loading…