HCID 24798571, compound → HCID 59589801, compound

HRID 1054426Notes

Reaction equation

HRID 1054426 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=O)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>O1CCCC1>[CH:21]1([CH2:19][NH:18][C:16]2[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[N:14]3[N:15]=2)[CH2:22][CH2:23]1

Participants

3

Reactant 1

HCID 24798571HCID 24798571, compound

Product 1

HCID 59589801HCID 59589801, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To cyclopropanecarboxylic acid [5-(4-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide (WW-005) ((0.07 g, 0.227 mmol), BH3 (1M in tetrahydrofuran, 1.2 mL, 1.2 mmol) was added dropwise and the mixture was stirred overnight. The reaction was quenched with methanol and the solvents were removed under reduced pressure. The crude product was purified by preparatory HPLC. LCMS method: 1, 4.45 min, MI: 295 [M+1]. 1H NMR (DMSO): 0.18-0.22 (m, 2H), 0.35-0.41 (m, 2H), 1.04-1.08 (m, 1H), 2.87 (t, 2H), 3.86 (s, 3H), 6.64 (t, 1H), 6.97 (d, 1H), 7.06 (d, 2H), 7.32 (d, 1H), 7.46 (t, 1H), 7.96 (d, 2H).

Workup

  1. customThe reaction was quenched with methanol
  2. customthe solvents were removed under reduced pressure
  3. customThe crude product was purified by preparatory HPLC
  4. custom1, 4.45 min, MI

Sources & evidence

ORD record
ord-cf370044b8ce4d3abcff5949bc9ce9d1
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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