Diisopropylethylamine → 4-[4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

HRID 1783988Notes

Reaction equation

HRID 1783988 reaction equation
CN1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36](Br)=[N:35][CH:34]=1.[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56]2[CH:61]=[CH:60][C:59]([NH2:62])=[CH:58][CH:57]=2)[C:52](=[O:63])[CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44].C(N(C(C)C)C(C)C)C>CC(O)C>[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56]2[CH:57]=[CH:58][C:59]([NH:62][C:36]3[C:37]4[N:38]([N:39]=[CH:40][N:41]=4)[C:33]([Br:32])=[CH:34][N:35]=3)=[CH:60][CH:61]=2)[C:52](=[O:63])[CH2:51]1)=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 57437534Tert-butyl 4-(4-aminophenyl)-3-oxopiperazine-1-carboxylateHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide

Product 1

HCID 866196644-[4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl esterYield 51.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This compound may be prepared using methods as described for Compound 6, step 1, using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.283 g, 1.00 mmol), 4-(4-amino-phenyl)-3-oxo-piperazine-1-carboxylic acid ter-t-butyl ester (0.300 g, 1.00 mmol) and N-ethyldiisopropyl-amine (0.20 mL, 1.02 mmol) in 2-propanol (1 mL). Purification of the crude material by silica gel column chromatography eluting with DCM followed by 98:2 DCM:MeOH affords 4-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester as a white solid (0.252 g, 51%).

Workup

  1. customThis compound may be prepared
  2. customPurification of the crude material by silica gel column chromatography
  3. washeluting with DCM

Sources & evidence

ORD record
ord-656a55838efe46668d7934a03825cb9b
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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