2-Chlorobenzothiazole → Butyl [5-(1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

HRID 1851780Notes

Reaction equation

HRID 1851780 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)COB([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])(C)C)=[N:22][CH:23]=2)OC1.CO[C:36]1C=CC2N=C(C3C=NC(N)=NC=3)SC=2[CH:37]=1>>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][NH:25][C:26](=[O:32])[O:27][CH2:28][CH2:31][CH2:36][CH3:37])=[N:22][CH:23]=1

Participants

4

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 248040695-(6-Methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amineHCID 86626541tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate

Product 1

HCID 86669117Butyl [5-(1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

Procedure

2-Chlorobenzothiazole (31 μL, 0.25 mmol) and tert-butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate (80 mg, 0.25 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine. After 1 h at 80° C., the mixture was concentrated under reduced pressure and the residue was partitioned between DCM and H2O. The organic phase was concentrated. Flash chromatography (Heptane/EtOAc gradient) gave the product (53 mg) as a white solid. MS m/z (M+H) 342.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between DCM and H2O
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-549f7295944c43f69f0188cd976aa27b
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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