Potassium Carbonate → HCID 25156760, compound

HRID 1686908Notes

Reaction equation

HRID 1686908 reaction equation
[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=2[C:29]([NH:31][CH3:32])=[O:30])=[N:4][C:5]([NH:8][C:9]2[CH:25]=[CH:24][C:12]3[CH2:13][CH2:14][N:15](C(=O)C(F)(F)F)[CH2:16][CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=2[C:29]([NH:31][CH3:32])=[O:30])=[N:4][C:5]([NH:8][C:9]2[CH:25]=[CH:24][C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 25157034HCID 25157034, compound

Product 1

HCID 25156760HCID 25156760, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{5-Chloro-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide (350 mg/0.67 mmol) was dissolved in methanol (5 mL) and treated with solid potassium carbonate (500 mg/3.2 mmol). The suspension was allowed to stir at room temperature overnight. The resulting opaque solution was concentrated and taken up in 10% methanol/methylene chloride. This mixture was filtered and concentrated to afford 2-[5-Chloro-2-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide as a yellow solid (200 mg/70%). 1H NMR (400 MHz, DMSO-d6) δ 11.52 (br s, 1H), 9.31 (s, 1H), 8.82-8.61 (m, 2H), 8.20 (s, 1H), 7.75 (d, J=7.6 Hz, 1H), 7.49-7.41 (m, 2H), 7.31 (d, J=8.0 Hz, 1H), 7.12 (m, 1H), 6.97 (d, J=8.0 Hz, 1H), 2.82-2.68 (m, 11H). LC/MS found 423 (M+H). mp 162-190° C. (dec.).

Workup

  1. concentrationThe resulting opaque solution was concentrated
  2. filtrationThis mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0676752166fd434ea42406373679eeb9
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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