Water → HCID 58344920, compound

HRID 1887989Notes

Reaction equation

HRID 1887989 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=[C:11]2[C:19]2[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:6][CH:5]=1.C(N(C(C)C)CC)(C)C.[N:35]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[C:36]=[O:37].O>C(Cl)Cl>[NH2:25][C:20]1[C:19]([C:11]2[N:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:3][NH:2][C:36]([NH:35][C:38]4[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=4)=[O:37])=[CH:9][CH:8]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 794431-Isocyanato-4-methoxybenzeneHCID 81531DiisopropylethylamineHCID 60155179HCID 60155179, compound

Product 1

HCID 58344920HCID 58344920, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(3-(4-(aminomethyl)phenyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine HCl salt (63 mg, 0.2 mmol) was suspended in DCM (2 mL). Diisopropylethylamine (0.07 mL, 0.4 mmol) was added. After everything went into solution 1-isocyanato-4-methoxybenzene (29 mg, 0.2 mmol) were added. After 20 minutes, water (5 mL) was added and diluted with dichloromethane. The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and it was purified by silica gel chromatography (0-20% methanol in dichloromethane) to yield the desired product (14 mg, 15% yield). Mp. 224-226° C.; 400 M Hz 1H NMR (CD3OD) δ: 8.36-8.28 (m, 1H), 8.22-8.15 (m, 1H), 8.0-7.92 (m, 1H), 7.56-7.47 (m, 2H), 7.46-7.36 (m, 3H), 7.36-7.29 (m, 1H), 7.29-7.22 (m, 2H), 6.89-6.81 (m, 2H), 6.5-6.42 (m, 1H), 4.47 (s, 2H), 3.75 (s, 3H); LCMS [M+H]: 466.

Workup

  1. additionwere added
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the solvent
  5. customwas removed under reduced pressure and it
  6. customwas purified by silica gel chromatography (0-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f14175a89aa7485d98ceb7fae1980304
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

Loading…