Cesium carbonate → HCID 49832654, compound

HRID 1947518Notes

Reaction equation

HRID 1947518 reaction equation
[Na].[N:2]1([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.Cl[C:20]1[S:21][C:22]2[C:23]([N:28]=1)=[N:24][CH:25]=[CH:26][N:27]=2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[N:2]1([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:20]4[S:21][C:22]5[C:23]([N:28]=4)=[N:24][CH:25]=[CH:26][N:27]=5)=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 574827642-Chlorothiazolo[4,5-b]pyrazineHCID 68771253HCID 68771253, compound

Product 1

HCID 49832654HCID 49832654, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-morpholin-4-ylmethyl-1H-indol-6-ol sodium salt (130 mg, 0.51 mmol) and 2-chloro-thiazolo[4,5-b]pyrazine (70 mg, 0.41 mmol) in DMF (1.4 mL) was added Cs2CO3 (43 mg, 0.12 mmol) and the resulting suspension was stirred (rt, 16 h). The reaction mixture was filtered and the solid was rinsed with EtOAc. The reaction mixture was concentrated in vacuo. The resulting residue was purified via reverse phase HPLC to provide the title compound as a white powder (38.3 mg, 26%). MS (ESI): mass calculated for C18H17N5O2S, 367.1; m/z found, 368.1 [M+H]+. 1H NMR (600 MHz, CDCl3): 8.51 (d, J=2.6, 1H), 8.32 (d, J=2.6, 1H), 8.21 (s, 1H), 7.83 (d, J=8.6, 1H), 7.45 (d, J=2.2, 1H), 7.21 (d, J=2.3, 1H), 7.12 (dd, J=8.6, 2.2, 1H), 3.75-3.69 (m, 6H), 2.51 (s, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was rinsed with EtOAc
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe resulting residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-454000d8d7b54872b7add10f25285fcb
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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