Dabco → HCID 57590026, compound

HRID 1783958Notes

Reaction equation

HRID 1783958 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:49]=[C:48]([N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)[CH:47]=[CH:46][C:45]=1[NH2:56].CCN(C(C)C)C(C)C.N12CCN(CC1)CC2>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:45]2[CH:46]=[CH:47][C:48]([N:50]3[CH2:51][CH2:52][O:53][CH2:54][CH2:55]3)=[CH:49][C:44]=2[F:43])=[N:35][CH:34]=1

Participants

7

Reactant 5

HCID 9237DabcoHCID 81531DiisopropylethylamineHCID 114810032-Fluoro-4-(4-morpholinyl)benzenamineHCID 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 57590026HCID 57590026, compound

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 (0.105 g, 0.89 mmol), 2-fluoro-4-morpholin-4-yl-phenylamine (93 mg, 0.474 mmol), DIPEA (0.123 mL, 0.706 mmol) and 1,4-diazabicyclo[2.2.2]octane (53 mg, 0.472 mmol) in 2-propanol (2 mL). The reaction mixture is partitioned between DCM and 10% citric acid (aq) solution, the organic layer is separated and washed with 10% citric acid solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo. The title compound is isolated as a pale red solid (77 mg, 42%) and used in the next step without further purification. LCMS: Rt 3.48 min (89%).

Workup

  1. customThis compound may be prepared
  2. customThe reaction mixture is partitioned between DCM and 10% citric acid (aq) solution
  3. customthe organic layer is separated
  4. washwashed with 10% citric acid solution, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac7bb6b97fb5453da4d1ade21276404c
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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