Cesium carbonate → HCID 51357948, compound

HRID 2077524Notes

Reaction equation

HRID 2077524 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[C:21]([NH2:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[C:24]1([C:21]([NH:30][C:2]2[N:7]=[C:6]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=4[CH:9]=3)[CH:5]=[CH:4][N:3]=2)([CH3:23])[CH3:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68509CumylamineHCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 51357948HCID 51357948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.1 g, 0.3 mmol), cumylamine (0.05 mL, 0.4 mmol), cesium carbonate (0.05 g, 0.7 mmol) in N,N-DMF was heated under microwave (CEM) at 180° C. for 20 min. The mixture was diluted with DCM and washed with water, dried over sodium sulfate, and concentrated. The residue was purified by HPLC (5-100% CH3CN in water with 0.05% TFA) to give N-(6-(2-(2-phenylpropan-2-ylamino)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide as an off-white solid. MS (ESI pos. ion) m/z: 404 (MH+). Calculated exact mass for C22H21N5OS: 403.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by HPLC (5-100% CH3CN in water with 0.05% TFA)

Sources & evidence

ORD record
ord-0f8c0b5fc6cd438fa89b8388d9691a37
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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