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Cesium carbonate → (2-Methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridin-4-yl)-(2-methyl-thiazol-4-yl)-amine

HRID 1443084
Notes
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Reaction equation

HRID 1443084 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][N:3]=1.[NH2:18][C:19]1[N:20]=[C:21]([CH3:24])[S:22][CH:23]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:11][C:9]1[S:10][C:6]2[C:5]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:4][N:3]=[C:2]([NH:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)[C:7]=2[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 147727002-Methyl-1,3-thiazol-4-amineHCID 866124154-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine

Product 1

HCID 16660577(2-Methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridin-4-yl)-(2-methyl-thiazol-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-2-methyl-7-pyridin-3-yl-thiazolo[4,5-c]pyridine (100 mg, 0.38 mmol) and 4-amino-2-methylthiazole (44 mg, 0.38 mmol) (Example C) were dissolved in 3 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (44 mg, 0.08 mmol) and cesium carbonate (200 mg, 0.61 mmol) were added and this mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Tris(dibenzylideneacetone)dipalladium chloroform complex (38 mg, 0.035 mmol) was added and the reaction mixture was stirred for 1 hour at 100° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient) and recrystallization in diisopropylether. The desired product was obtained as a yellow solid (20 mg, 15%), MS: m/e 354.1 (M+H+).

Workup

  1. customthis mixture was evacuated
  2. customto remove oxygen from the solution
  3. additionTris(dibenzylideneacetone)dipalladium chloroform complex (38 mg, 0.035 mmol) was added
  4. customThe reaction mixture was then evaporated
  5. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient) and recrystallization in diisopropylether

Sources & evidence

ORD record
ord-e27c29bee49b45af9edf22c6e14e31cf
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07659401B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes