Imidazole → HCID 178434297, compound

HRID 2375925Notes

Reaction equation

HRID 2375925 reaction equation
Br[CH2:2][CH2:3][C:4]([OH:6])=O.[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([NH:29][C:30]3[C:31]4[CH:38]=[C:37]([C:39]5[CH2:40][CH2:41][NH:42][CH2:43][CH:44]=5)[NH:36][C:32]=4[N:33]=[CH:34][N:35]=3)[CH:27]=2)[NH:22][N:21]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[N:7]1([CH2:2][CH2:3][C:4]([N:42]2[CH2:43][CH:44]=[C:39]([C:37]3[NH:36][C:32]4[N:33]=[CH:34][N:35]=[C:30]([NH:29][C:26]5[CH:27]=[C:28]6[C:23](=[CH:24][CH:25]=5)[NH:22][N:21]=[C:20]6[CH3:19])[C:31]=4[CH:38]=3)[CH2:40][CH2:41]2)=[O:6])[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

8

Reactant 6

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 115533-Bromopropionic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178434294HCID 178434294, compound

Product 1

HCID 178434297HCID 178434297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

β-Bromopropionic acid (29.1 mg, 0.190 mmol), 1H-imidazole (19.4 mg, 0.286 mmol), potassium carbonate (160 mg, 1.16 mmol) and DMF (3 mL) was combined together and stirred at rt for 20 h. After that time, (3-methyl-1H-indazol-5-yl)-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine hydrogen chloride tri-salt (122 mg, 0.190 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (76.7 mg, 0.400 mmol), and 1-hydroxybenzotriazole (27.0 mg, 0.200 mmol) was added into the above reaction mixture and was stirred at rt under an atmosphere of N2 for 24 h. After that time, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in DMSO for submission to MS-directed purification to obtain the title compound as beige oil. 1H NMR (DMSO-d6, 400 MHz): δ=2.54-2.56 (m, 2H), 2.59 (s, 3H), 2.97-3.07 (m, 2H), 3.73 (t, 1H, J=5.2 Hz), 3.80 (t, 1H, J=5.6 Hz), 4.25 (brs, 2H), 4.30-4.33 (m, 2H), 6.48 (d, 1H, J=4.0 Hz), 6.80 (d, 1H, J=18.8 Hz), 6.94 (d, 1H, J=0.8 Hz), 7.28-7.30 (m, 1H), 7.52 (d, 1H, J=8.8 Hz), 7.73 (t, 1H, J=0.8 Hz), 7.76-7.80 (m, 1H), 8.23 (dd, 1H, J=1.2 & 6.8 Hz), 8.32 (d, 1H, J=2.0 Hz), 9.40 (s, 1H), 12.01 (brs, 1H), 12.56 (brs, 1H). MS (ES+): m/z 468.11 (10) [MH+]. HPLC: tR=1.62 min (ZQ2000, polar—5 min).

Workup

  1. stirringwas stirred at rt under an atmosphere of N2 for 24 h
  2. filtrationAfter that time, the mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in DMSO for submission to MS-directed purification

Sources & evidence

ORD record
ord-5766cf26efc6451e985f586c47fa5670
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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