Triethylamine → HCID 67391050, compound

HRID 906442Notes

Reaction equation

HRID 906442 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[NH:28][CH:27]=[C:26]2[S:34](Cl)(=[O:36])=[O:35]>C1COCC1>[Br:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[NH:28][CH:27]=[C:26]2[S:34]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 574399006-Bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride

Product 1

HCID 67391050HCID 67391050, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 1,4-diazepane-1-carboxylate (0.621 g) and triethylamine (0.864 mL) in THF (12 mL) was added dropwise a solution of 6-bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride (Example 46a, 1 g) in THF (20 mL). The reaction was stirred at room temperature for 20 min. The resulting solution was concentrated under reduced pressure, acidified with 2 M HCl, and extracted into ethyl acetate. The combined organics were dried (MgSO4), filtered and evaporated under reduced pressure to give the subtitle compound (1.097 g) that was used without further purification.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. extractionextracted into ethyl acetate
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d40b05ca164147fabfb0fb1ea4d392dc
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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