945400-88-4 → Tert-butyl (5-{6-[(tert-butoxycarbonyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)methylcarbamate

HRID 1698108Notes

Reaction equation

HRID 1698108 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)COB([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[N:30][CH:31]=2)OC1.C(OC(=O)NCC1C=CC(C2SC3C=C(C(=O)N)C=CC=3N=2)=CN=1)(C)(C)C>>[C:14]([O:13][C:12]([NH:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:26]3[CH:27]=[CH:28][C:29]([CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[N:30][CH:31]=3)[S:3][C:4]=2[CH:10]=1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 57553402945400-88-4HCID 86626541tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamateHCID 86626543Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

Product 1

HCID 86626544Tert-butyl (5-{6-[(tert-butoxycarbonyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)methylcarbamateYield 80.3%

Procedure

tert-Butyl (2-bromo-1,3-benzothiazol-6-yl)carbamate (100 mg, 0.30 mmol) and tert-butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate (0.146 g, 0.46 mmol) were subjected to the procedure used for the preparation of tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate. This gave the product (110 mg) as a white solid. MS m/z (M−H) 455.

Sources & evidence

ORD record
ord-f3fcbabf844a45c8b20b78d872a17c67
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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