Triethylamine → HCID 57900243, compound

HRID 627971Notes

Reaction equation

HRID 627971 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([NH:17][NH2:18])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:19]=1.C(N(CC)CC)C.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]4[O:16][C:32](=[O:33])[NH:18][N:17]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-Carbonyldiimidazole2×HCID 57900326HCID 57900326, compound

Product 1

HCID 57900243HCID 57900243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazide (150 mg, 0.44 mmol) was suspended in tetrahydrofuran (5.0 mL) and triethylamine (0.12 mL, 0.88 mmol) was added. N,N-Carbonyldiimidazole (108 mg, 0.66 mmol) was added and the whole stirred at room temperature for 1 h. No reaction was observed. The whole was sealed and heat at 80° C. for 2 h. More N,N-carbonyldiimidazole (150 mg, 0.92 mmol) was added and the whole heated at 85° C. for 10 min. LCMS indicated clean conversion to the desired product. The reaction mixture was cooled to room temperature, diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organics were dried over sodium sulfate. Concentration gave 125 mg colorless solid. A small amount was purified by reverse phase HPLC to give 266 as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ 11.99 (br s, 1H), 7.70-7.00 (overlapping m, 4H), 4.23 (t, 2H), 3.21 (t, 2H). MS: (ESI+) 367.0

Workup

  1. customThe whole was sealed
  2. temperatureheat at 80° C. for 2 h
  3. temperaturethe whole heated at 85° C. for 10 min

Sources & evidence

ORD record
ord-6a76bee3c04e4cf0957be49b5d9d2ca7
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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