Pyridine → HCID 59110594, compound

HRID 460264Notes

Reaction equation

HRID 460264 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[S:18][CH:19]=[C:20](C(O)=O)[N:21]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])=CC=1.[N:42]1([CH2:48][C:49]2[N:54]=[C:53]([NH2:55])[CH:52]=[CH:51][CH:50]=2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1.[N:56]1[CH:61]=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[S:18][CH:19]=[C:20]([NH:56][C:61]([NH:55][C:53]4[CH:52]=[CH:51][CH:50]=[C:49]([CH2:48][N:42]5[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]5)[N:54]=4)=[O:32])[N:21]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 199401P,P-Diphenylphosphinic azideHCID 187716712-Amino-6-(piperidin-1-ylmethyl)pyridineHCID 694111395-(4-Carboxy-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 59110594HCID 59110594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-(4-carboxy-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester (2.65 g, 7.69 mmol), molecular sieves, and 100 mL of dry toluene was added TEA (1.6 mL, 11.5 mmol). The resulting solution was stirred for 20 min then DPPA (2.5 mL, 11.6 mmol) was added and the resulting solution was stirred at 80° C. for 40 min. 6-Piperdin-1-ylmethyl-pyridin-2-ylamine (1.64 g, 8.6 mmol) and pyridine (1.0 mL, 12.4 mmol) were added and the mixture was stirred at 80° C. for another 14 h. The molecular sieves were filtered off and washed with CH2Cl2 and MeOH. The filtrate was concentrated in vacuo and the resulting residue was purified by flash chromatography on silica gel using 3% MeOH/CH2Cl2 to give a brown solid. MS m/z: 533 (M+1). Calc'd for C28H32N6O3S-532.66.

Workup

  1. stirringthe resulting solution was stirred at 80° C. for 40 min
  2. stirringthe mixture was stirred at 80° C. for another 14 h
  3. filtrationThe molecular sieves were filtered off
  4. washwashed with CH2Cl2 and MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting residue was purified by flash chromatography on silica gel using 3% MeOH/CH2Cl2
  7. customto give a brown solid

Sources & evidence

ORD record
ord-9172118bbfb649bd989c575ddf60c8e8
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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