Sodium Bicarbonate → N-(2-chloro-5-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

HRID 2077606Notes

Reaction equation

HRID 2077606 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.Br[C:30]1[CH:46]=[CH:45][C:33]2[N:34]=[C:35]([NH:37][CH2:38][CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[S:36][C:32]=2[CH:31]=1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[CH:6][C:5]([C:30]2[CH:46]=[CH:45][C:33]3[N:34]=[C:35]([NH:37][CH2:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[S:36][C:32]=3[CH:31]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 57416510N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-methoxybenzenesulfonamideHCID 772315086-bromo-N-(cyclohexylmethyl)benzo[d]thiazol-2-amine

Product 1

HCID 57585024N-(2-chloro-5-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A reaction tube was charged with N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (157 mg, 0.369 mmol), 6-bromo-N-(cyclohexylmethyl)benzo[d]thiazol-2-amine (80 mg, 0.246 mmol), Pd(PPh3)4 (14.2 mg, 0.012 mmol), 2.0 M aqueous sodium bicarbonate (0.246 mL, 0.492 mmol) and 0.98 mL ethanol. The tube was sealed and the mixture was heated at 85° C. for 2.5 h. The reaction was concentrated, dissolved in 90/10 CH2Cl2/MeOH and passed through a silica plug. The filtrates were concentrated and the crude material was purified by reverse phase chromatography to provide N-(2-chloro-5-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide as a slightly yellow solid (7 mg, 5.2%). MS (ESI pos. ion) m/z calc'd for C21H27ClN4O3S2: 543.1/545.1. found 543.0/545.0.

Workup

  1. customThe tube was sealed
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in 90/10 CH2Cl2/MeOH
  4. concentrationThe filtrates were concentrated
  5. customthe crude material was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-9876df00a8cf46069863a7636fba785d
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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