Bromide ion → HCID 86281290, compound

HRID 930828Notes

Reaction equation

HRID 930828 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([NH:18][C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:20])[CH:14]=[CH:15][C:16]=3[Cl:17])[N:10]=2)[CH:7]=1.[Br-].[CH3:27][O:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)=[O:30]>CO>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([NH:18][C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[CH:12][C:11]=1[C:9]1[N:10]=[C:5]2[N:4]=[CH:3][C:2]([C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:29](=[O:30])[O:28][CH3:27])=[CH:37][CH:36]=3)=[CH:7][N:6]2[CH:8]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 27734944-(Methoxycarbonylamino)phenylboronic acidHCID 90412061HCID 90412061, compound

Product 1

HCID 86281290HCID 86281290, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 24 was synthesized using N-(3-(6-bromoimidazo[1,2-a]pyrimidin-2-yl)-4-chlorophenyl)pyrrolidine-1-carboxamide (I-15) as the bromide and (4-((methoxycarbonyl)amino)phenyl)boronic acid using a suzuki coupling protocol as described in the synthesis of I-11. The residue was redissolved in methanol and precipitation yielded the compound. m/z (ESI) of 24: 491.2 (M+H+), 1H NMR (600 MHz, DMSO-D6) δ 9.86 (s, 1H), 9.30 (d, J=2.6, 1H), 8.94 (d, J=2.6, 1H), 8.55 (s, 1H), 8.47 (d, J=2.8, 2H), 7.73 (m, 3H), 7.62 (d, J=8.5, 2H), 7.41 (d, J=8.8, 1H), 3.70 (s, 3H), 3.40 (t, J=6.5, 4H), 1.86 (t, J=6.4, 4H).

Workup

  1. customas described in the synthesis of I-11
  2. customprecipitation
  3. customyielded the compound

Sources & evidence

ORD record
ord-e2b78c93d71d49309b6bd76f6ef91a7f
Source dataset
uspto-grants-2016_03
Patent number
US09296754B2

Reaction notes

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