Methyl Glycolate → Methyl 3-amino-6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylfuro[2,3-b]pyridine-2-carboxylate

HRID 1869276Notes

Reaction equation

HRID 1869276 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[NH:27][C:26]5[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:25]=5[N:24]=4)[CH2:19][CH2:18]3)=[CH:12][CH:11]=2)[C:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:6][C:3]=1[C:4]#[N:5].ClC1N=C(C2C=CC(CN3CCC(N4C5C=CC=CC=5NC4=O)CC3)=CC=2)C(C2C=CC=CC=2)=CC=1C#N.[C:77]([O:81][CH3:82])(=[O:80])[CH2:78][OH:79].C[O-].[K+]>CN(C=O)C>[NH2:5][C:4]1[C:3]2[C:2](=[N:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([CH2:16][N:17]4[CH2:22][CH2:21][CH:20]([C:23]5[NH:27][C:26]6[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:25]=6[N:24]=5)[CH2:19][CH2:18]4)=[CH:14][CH:15]=3)=[C:7]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:6]=2)[O:79][C:78]=1[C:77]([O:81][CH3:82])=[O:80]

Participants

6

Reactant 4

HCID 66774Methyl GlycolateHCID 111799672-chloro-6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrileHCID 114098042-Chloro-6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl]-5-phenylnicotinonitrileHCID 23664618Potassium methoxide

Product 1

HCID 11387596Methyl 3-amino-6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylfuro[2,3-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 2-chloro-6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (3-1, synthesis made in a similar manner as shown in Scheme 1, compound 1-6; 0.026 g, 0.05 mmol), methyl glycolate (0.01 g, 0.11 mmol) and potassium methoxide (0.009 mg, 0.11 mmol) in DMF (1 mL) was heated to 70° C. for 1 h. The mixture was purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) to give Methyl 3-amino-6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylfuro[2,3-b]pyridine-2-carboxylate (3-2). LRMS m/z (M+H) Calcd: 576.6, found: 576.2.

Workup

  1. customThe mixture was purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-90213e7dbf6b42ebb5c0a52c78615050
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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