Hydrogen Bromide → HCID 178439970, compound

HRID 1458422Notes

Reaction equation

HRID 1458422 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([OH:16])=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2].Br.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28](O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:1]([C:4]1[NH:8][C:7]2[CH:9]=[C:10]([O:16][CH:28]3[CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:26][CH2:27]3)[C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 22100814HCID 22100814, compound

Product 1

HCID 178439970HCID 178439970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-isopropyl-6-hydroxy-5-nitrobenzimidazole and the HBr addition product (15 g), N-tert-butoxycarbonyl-4-hydroxypiperidine (17.7 g), PPh3 (23.1 g), and THF (150 mL) at room temperature was added DEAD (14 mL). After 4 hours, the solvent was removed in vacuo and the product recovered from the crude using chromatography (3% methanol/methylene chloride) to yield 2-isopropyl-5-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-6-nitrobenzimidazole (16.5 g).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe product recovered from the crude

Sources & evidence

ORD record
ord-b1d1e29c521b49bdb7d537fc0726163f
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

Loading…