Triethylamine → HCID 57773637, compound

HRID 333123Notes

Reaction equation

HRID 333123 reaction equation
Cl.[NH2:2][CH:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[I:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>ClCCl>[I:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:2][CH:3]2[C:11]3[C:6](=[CH:7][C:8]([S:12](=[O:13])(=[O:14])[NH2:15])=[CH:9][CH:10]=3)[CH2:5][CH2:4]2)=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 68630202HCID 68630202, compound

Product 1

HCID 57773637HCID 57773637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing 1-amino-2,3-dihydro-1H-indene-5-sulfonamide hydrochloride salt (93 mg, 0.38 mmol) suspended in dichloromethane (3 mL) was added triethylamine (61 μL) followed by 4-iodobenzoylchloride (100 mg, 0.38 mmol) and the reaction was stirred overnight at room temperature. The reaction was diluted with dischloromethane (25 mL) and washed with 10% aqueous hydrochloric acid (10 mL), water (10 mL), brine (10 mL), dried over sodium sulfate and concentrated to afford the crude material as an off-white solid. Recrystallization from ethanol/water afforded MIP-1146 (19 mg, 21%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.96 (m, 2H), 7.85-7.35 (m, 8H), 5.60 (m, 1H), 3.15-2.75 (m, 2H), 2.15-1.90 (m, 2H); (M+H)+ (443).

Workup

  1. additionThe reaction was diluted with dischloromethane (25 mL)
  2. washwashed with 10% aqueous hydrochloric acid (10 mL), water (10 mL), brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7ab8d123285749b492c39b32ae227aef
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

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