tert-Butyl piperazine-1-carboxylate → 4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2190639Notes

Reaction equation

HRID 2190639 reaction equation
Cl[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][N:15]3[CH2:18][CH3:19])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[C:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(OC(N1CCN(C2C=CC(C(=O)NC3C=CC(C)=C(I)C=3)=CN=2)CC1)=O)(C)(C)C>>[C:25]([O:24][C:22]([N:29]1[CH2:34][CH2:33][N:32]([C:2]2[CH:21]=[CH:20][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:17]=[C:16]4[C:12]([CH:13]=[CH:14][N:15]4[CH2:18][CH3:19])=[CH:11][CH:10]=3)=[CH:4][N:3]=2)[CH2:31][CH2:30]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 59317999HCID 59317999, compoundHCID 593181844-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593180064-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Procedure

4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester was prepared from 6-chloro-N-(1-ethyl-1H-indol-6-yl)-nicotinamide and 1-Boc-piperazine following a method similar to the one described in the synthesis of 4-[5-(3-iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester above. The product was obtained after silica gel column purification with 10-30% Et2O in toluene gradient. HRMS m/z calcd for C25H31N5O3 [M+H]+: 450.2500. Found: 450.2497.

Workup

  1. customThe product was obtained
  2. customafter silica gel column purification with 10-30% Et2O in toluene gradient

Sources & evidence

ORD record
ord-1a602d8acc0f45f1b3ad840b8de125c4
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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