Hydrochloric Acid → 2-(3,4-Dichlorophenyl)-3-(1H-imidazol-4-yl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one

HRID 1192452Notes

Reaction equation

HRID 1192452 reaction equation
Cl.Cl.[N:3]1([C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]([CH2:30][C:31]2[N:32]=[CH:33][NH:34][CH:35]=2)[C:27](O)=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25].Cl>CCOCC>[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]([CH2:30][C:31]2[N:32]=[CH:33][NH:34][CH:35]=2)[C:27]([N:6]2[CH2:5][CH2:4][N:3]([C:9]3[C:10]4[CH:17]=[CH:16][NH:15][C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:8][CH2:7]2)=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 675378564-(Piperazin-1-yl)-1H-pyrrolo[2,3-d]pyrimidine dihydrochlorideHCID 1785253572-(3,4-Dichlorophenyl)-3-(1H-imidazol-4-yl)-propionic acid

Product 1

HCID 1785205102-(3,4-Dichlorophenyl)-3-(1H-imidazol-4-yl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(3,4-Dichlorophenyl)-3-(1H-imidazol-4-yl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one was prepared by substituting 5-piperazin-1-yl-1H-indazole with 4-Piperazin-1-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride and substituting (D)-Boc-4-chlorophenylalanine with 2-(3,4-Dichlorophenyl)-3-(1H-imidazol-4-yl)-propionic acid in Example B-1, Step 2. The free amine was converted to HCl salt by treatment with HCl in Ether. 1H NMR (CD3OD, 400 MHz) δ 8.76 (s, 1H), 8.32 (s, 1H), 7.52 (m, 2H), 7.38 (s, 1H), 7.29 (m, 2H), 6.92 (s, 1H), 4.58 (m, 1H), 3.70-4.20 (m, 7H), 3.63 (m, 1H), 3.43 (m, 1H), 3.16 (m, 1H). LCMS (APCI+) m/z 470, 472, 474 [M+H]+; Rt=2.15 min.

Sources & evidence

ORD record
ord-2763e08bc5874f889cb958ccb1dff582
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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