Diisopropylethylamine → 5-Bromo-N-[4-(4-tert-butylpiperazin-1-yl)phenyl][1,2,4]triazolo[1,5-a]pyrazin-8-amine

HRID 1783993Notes

Reaction equation

HRID 1783993 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]([N:47]1[CH2:52][CH2:51][N:50]([C:53]2[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=2)[CH2:49][CH2:48]1)([CH3:46])([CH3:45])[CH3:44].C(N(C(C)C)C(C)C)C>CC(O)C>[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:59][C:56]2[CH:55]=[CH:54][C:53]([N:50]3[CH2:49][CH2:48][N:47]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:52][CH2:51]3)=[CH:58][CH:57]=2)=[N:35][CH:34]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 242791824-(4-tert-Butylpiperazin-1-yl)anilineHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 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 575899945-Bromo-N-[4-(4-tert-butylpiperazin-1-yl)phenyl][1,2,4]triazolo[1,5-a]pyrazin-8-amineYield 92.4%

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 (0.308 g, 1.107 mmol), 4-(4-tert-butyl-piperazin-1-yl)-phenylamine (0.310 g, 1.33 mmol) and N-ethyldiisopropyl-amine (0.289 mL, 1.66 mmol) in 2-propanol (5 mL). The reaction mixture is partitioned between DCM and 1N NaOH, the organic layer is separated and washed with water and brine, dried over MgSO4, filtered and concentrated under vacuum. Trituration of the residue with diethyl ether and petroleum ether affords the title compound (440 mg, 92%) as a cream solid. LCMS: Rt 2.25 min (96%).

Workup

  1. customThis compound may be prepared
  2. customThe reaction mixture is partitioned between DCM and 1N NaOH
  3. customthe organic layer is separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6e039fcd201442198ed4aec7b55f7875
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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