Potassium Carbonate → HCID 66786854, compound

HRID 1947543Notes

Reaction equation

HRID 1947543 reaction equation
Cl.Cl.[C@H:3]12[CH2:9][C@H:6]([NH:7][CH2:8]1)[CH2:5][N:4]2[CH2:10][C:11]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][C:21]3[S:22][C:23]4[C:24]([N:29]=3)=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:19][C:14]=2[O:13][CH:12]=1.[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:7]2[CH2:8][C@@H:3]3[CH2:9][C@H:6]2[CH2:5][N:4]3[CH2:10][C:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[S:22][C:23]5[C:24]([N:29]=4)=[N:25][CH:26]=[CH:27][CH:28]=5)=[CH:19][C:14]=3[O:13][CH:12]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 66787015HCID 66787015, compound

Product 1

HCID 66786854HCID 66786854, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (1S,4S)-2-[3-(2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-benzofuran-6-yloxy]-thiazolo[4,5-b]pyridine dihydrochloride (50 mg, 0.11 mmol), 4-bromomethyl-benzoic acid methyl ester (28 mg, 0.12 mmol), and K2CO3 (38 mg, 0.28 mmol) in CH3CN (0.4 mL) was stirred at rt. Upon reaction completion, the mixture was concentrated, re-dissolved in DMF and purified by reverse phase HPLC to provide the title compound (10 mg, 16%). MS (ESI): mass calculated for C29H26N4O4S, 526.17; m/z found, 527.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.05-7.96 (m, 3H), 7.77 (d, J=8.5, 1H), 7.58 (dd, J=7.8, 4.3, 2H), 7.45 (d, J=8.3, 2H), 7.32-7.28 (m, 1H), 7.21 (dd, J=7.9, 4.8, 1H), 3.91 (s, 3H), 3.90-3.69 (m, 2H), 3.41-3.27 (m, 2H), 2.96-2.90 (m, 1H), 2.85-2.81 (m, 1H), 2.74-2.66 (m, 2H), 1.77 (s, 2H), 1.47 (s, 2H).

Workup

  1. customUpon reaction completion
  2. concentrationthe mixture was concentrated
  3. dissolutionre-dissolved in DMF
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-e98890b6ea7c4d50bc5e1befcc11d5c2
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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