3-Pyridinemethanamine → 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl benzamide
Reaction equation
OC1C=CC(CNC(=O)C2C=CC(NC3C4[N:18]([CH:27]=[CH:28]N=4)[C:19]([C:22]4[CH:23]=[N:24]N[CH:26]=4)=CN=3)=CC=2)=CC=1.[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37]([NH:43][C:44]2[CH:52]=[CH:51][C:47]([C:48]([OH:50])=O)=[CH:46][CH:45]=2)=[N:36][CH:35]=1.NCC1C=NC=CC=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C>[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37]([NH:43][C:44]2[CH:45]=[CH:46][C:47]([C:48]([NH:24][CH2:23][C:22]3[CH:19]=[N:18][CH:27]=[CH:28][CH:26]=3)=[O:50])=[CH:51][CH:52]=2)=[N:36][CH:35]=1Participants
7
Reactant 5
HCID 310183-Pyridinemethanamine
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 24857547N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide
HCID 582288294-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino) benzoic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
In the same way as described for Compound 90, step 3, using 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)benzoic acid (365 mg, 1.57 mmol), 3-aminomethylpyridine (0.16 mL, 1.57 mmol), N,N-diisopropylethylamine (0.42 mL, 2.35 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (715 mg, 1.9 mmol) and DMF (6 mL). The crude residue is purified using column chromatography, eluting with EtOAc followed by EtOAc:MeOH (95:5) then EtOAc:NH3 (7M in MeOH). The title amide is isolated as a solid.
Workup
- customThe crude residue is purified
- washeluting with EtOAc
Sources & evidence
- ORD record
- ord-437fb23679cb45d9be6f4b45b2101bce
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178530B2
Reaction notes
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