Diisopropylethylamine → (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(3-fluoro-4-morpholin-4-yl-phenyl)-amine

HRID 605906

Reaction equation

HRID 605906 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.[F:43][C:44]1[CH:45]=[C:46]([NH2:56])[CH:47]=[CH:48][C:49]=1[N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.CCN(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:56][C:46]2[CH:47]=[CH:48][C:49]([N:50]3[CH2:51][CH2:52][O:53][CH2:54][CH2:55]3)=[C:44]([F:43])[CH:45]=2)=[N:35][CH:34]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 14853303-Fluoro-4-morpholinoanilineHCID 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 57589997(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(3-fluoro-4-morpholin-4-yl-phenyl)-amineYield 98.5%

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 (0.5 g, 1.799 mmol), 3-fluoro-4-morpholin-4-yl-phenylamine (0.53 g, 2.70 mmol), and DIPEA (0.470 mL, 2.70 mmol) in 2-propanol (6 mL). The reaction mixture is partitioned between 10% citric acid aqueous solution and DCM. The organic phase is separated and washed with water and brine, dried over MgSO4, filtered and concentrated under vacuum to afford the title compound (697 mg, 98%) which is used in the next step without further purification. LCMS: Rt 3.52 min (98.2%).

Workup

  1. customThis compound may be prepared
  2. customThe reaction mixture is partitioned between 10% citric acid aqueous solution and DCM
  3. customThe organic phase 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-27112b23025d4d1797f595b435c6a5de
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Linked notes

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