Hydrochloric Acid → HCID 86297148, compound

HRID 930832Notes

Reaction equation

HRID 930832 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[C:17]1[N:18]=[C:19]2[N:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([N:31](C)[C:32](=O)OC(C)(C)C)=[CH:27][CH:26]=3)=[CH:21][N:20]2[CH:40]=1.Cl.O1CCOCC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[C:17]1[N:18]=[C:19]2[N:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([NH:31][CH3:32])=[CH:27][CH:26]=3)=[CH:21][N:20]2[CH:40]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131735151HCID 131735151, compound

Product 1

HCID 86297148HCID 86297148, compound

Conditions

Temperature
50 °C

Procedure

tert-butyl (4-(2-(2-chloro-5-(5-methylfuran-2-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)phenyl)(methyl)carbamate was treated with 4.0M HCl in dioxane (2 eq.) and was stirred overnight at 50° C. At completion, the reaction mixture was concentrated in vacuo and the residue was redissolved in methanol. Purification of the compound was done via mass-triggered reverse phase column chromatography preparative system (15% to 65% (B)), m/z (ESI) for 33: 460 (M+H+), 1H NMR (400 MHz, DMSO-D6) δ 10.32 (s, 1H), 9.19 (d, J=2.5, 1H), 8.90 (d, J=2.5, 1H), 8.69 (d, J=2.6, 1H), 8.56 (s, 1H), 7.93 (dd, J=2.7, 8.8, 1H), 7.53 (dd, J=1.7, 8.7, 3H), 7.34 (d, J=3.3, 1H), 6.68 (d, J=8.7, 2H), 6.35 (d, J=3.3, 1H), 6.00 (q, J=4.9, 1H), 2.73 (d, J=5.0, 3H), 2.40 (s, 3H).

Workup

  1. concentrationAt completion, the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was redissolved in methanol
  3. customPurification of the compound

Sources & evidence

ORD record
ord-9c2fe2e6e6e341e2b2e85d2dbb290890
Source dataset
uspto-grants-2016_03
Patent number
US09296754B2

Reaction notes

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