Triphenylphosphine → 1-cyclopropyl-3-((1-(4-fluorobutyl)-1H-imidazo[4,5-b]pyridin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 1424496Notes

Reaction equation

HRID 1424496 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]1[CH2:15]O.[CH:17]1([N:20]2[C:28]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[NH:22][C:21]2=[O:29])[CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O-])=O)=NC([O-])=O>C1COCC1>[CH:17]1([N:20]2[C:28]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[N:22]([CH2:15][C:7]3[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][F:1])[C:14]4[C:9]([N:8]=3)=[N:10][CH:11]=[CH:12][CH:13]=4)[C:21]2=[O:29])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 223493611-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-oneHCID 51573101N-carboxylatoiminocarbamateHCID 67991782(1-(4-fluorobutyl)-1H-imidazo[4,5-b]pyridin-2-yl)methanol

Product 1

HCID 679755321-cyclopropyl-3-((1-(4-fluorobutyl)-1H-imidazo[4,5-b]pyridin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-oneYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (1-(4-fluorobutyl)-1H-imidazo[4,5-b]pyridin-2-yl)methanol 42-5 (958 mg, 4.3 mmol), 1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one 10-d (950 mg, 5.15 mmol) and triphenylphosphine (1350 mg, 5.15 mmol) in 30 ml dry THF was added (E)-diïsopropyl diazene-1,2-dicarboxylate (1.26 ml, 6.43 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The precipitate was filtered off and washed with some diethyl ether to obtain the title product as a white powder (1036 mg, 63%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with some diethyl ether

Sources & evidence

ORD record
ord-05dba1f719f54b228c812e8da763c73e
Source dataset
uspto-grants-2015_01
Patent number
US08927720B2

Reaction notes

Loading…