tert-Butyl bromoacetate → tert-butyl 2-{3-carbamoyl-2-[3-(4-chlorophenyl)ureido]-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl}acetate

HRID 1483207Notes

Reaction equation

HRID 1483207 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:30])[NH:17][C:18]2[S:26][C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:20]=3[C:19]=2[C:27]([NH2:29])=[O:28])=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>O1CCCC1.C(Cl)Cl>[C:27]([C:19]1[C:20]2[CH2:25][CH2:24][N:23]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:22][C:21]=2[S:26][C:18]=1[NH:17][C:16]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=1)=[O:30])(=[O:28])[NH2:29]

Participants

6

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 1182698802-[3-(4-Chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide trifluoroacetate

Product 1

HCID 118307294tert-butyl 2-{3-carbamoyl-2-[3-(4-chlorophenyl)ureido]-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl}acetateYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound A4 (300 mg, 0.646 mmol), diisopropylethylamine (0.350 mL, 1.97 mmol), and tert-butyl 2-bromoacetate (0.140 mL, 0.950 mmol) in tetrahydrofuran (4 mL) was stirred at room temperature for 8 h. After this time, the reaction mixture was diluted with methylene chloride (10 mL), sonicated, and filtered to afford compound E1 as a light yellow solid (191 mg, 64%): 1H NMR (500 MHz, DMSO-d6) δ 10.93 (s, 1H), 10.18 (s, 1H), 7.59-7.29 (m, 5H), 6.89 (bs, 1H), 3.61 (s, 2H), 3.30 (s, 2H), 2.82-2.76 (m, 4H), 1.43 (s, 9H). MS (M+H) 465.

Workup

  1. customsonicated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a9e7760c69c3439fa3eedd0f377c7a44
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Reaction notes

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