Methylamine → HCID 53329872, compound

HRID 517961Notes

Reaction equation

HRID 517961 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=3)[N:7]=[C:6]([C:30]#[N:31])[C:5]=2[N:4]=[N:3]1.[C:32](Cl)(=[O:43])OC1C=CC([N+]([O-])=O)=CC=1.[CH3:45][NH2:46]>ClCCl>[C:30]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][N:23]([C:32]([NH:46][CH3:45])=[O:43])[CH2:24][CH2:25]3)=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=2)[CH:9]=[C:10]2[N:2]([CH3:1])[N:3]=[N:4][C:5]=12)#[N:31]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 821294-Nitrophenyl chloroformateHCID 67294093HCID 67294093, compound

Product 1

HCID 53329872HCID 53329872, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (50 mg) and 4-nitrophenyl carbono-chloridate (23 mg) were combined in dichloromethane and the reaction mixture stirred at room temperature for an hour. Methylamine (0.290 ml) was added and the reaction mixture stirred for 3 hours. Washed with water, the organic layer was separated, dried, and blown down to afford crude product. Purified by acidic prep HPLC to afford the title compound (8.1 mg).

Workup

  1. stirringthe reaction mixture stirred for 3 hours
  2. washWashed with water
  3. customthe organic layer was separated
  4. customdried
  5. customto afford crude product
  6. customPurified by acidic prep HPLC

Sources & evidence

ORD record
ord-2a45dafa8a134738a8c24086eabdae6d
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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