1-Propanol → HCID 178450642, compound

HRID 230027Notes

Reaction equation

HRID 230027 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([OH:38])=[CH:37][C:30]=3[N:29]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:39](O)[CH2:40][CH3:41].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClCCl>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]([C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([O:38][CH2:39][CH2:40][CH3:41])=[CH:37][C:30]=3[N:29]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 10311-PropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178450640HCID 178450640, compound

Product 1

HCID 178450642HCID 178450642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of butyl 1-[(trans-4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1H-benzimidazol-2-yl)amino]indane-5-carboxylate (49.0 mg, 0.095 mmol) in dry dichloromethane was added 1-propanol (18.0 □L, 0.24 mmol), diisopropyl azodicarboxylate (37.0 μL, 0.19 mmol) and Ph3P (50.0 mg, 0.19 mmol). After stirring at room temperature for 2 h, solvent was removed. Chromatography (15% EtOAc in Hexane) afforded butyl 1-[(trans-4-tert-butylcyclohexyl)(1-methyl-5-propoxy-1H-benzimidazol-2-yl)amino]indane-5-carboxylate. HPLC/MS: m/z=560.5 (M+1), Rt=2.43 min.

Workup

  1. customsolvent was removed

Sources & evidence

ORD record
ord-7f200aa56a384152a894add3e07b0d30
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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