Triethylamine → Tert-butyl 4-(isoquinolin-5-ylsulfonyl)-1,4-diazepane-1-carboxylate

HRID 251802Notes

Reaction equation

HRID 251802 reaction equation
Cl.[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[N:16]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(Cl)Cl>[C:26]([O:25][C:23]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([S:12]([C:7]2[C:6]3[CH:5]=[CH:4][N:3]=[CH:2][C:11]=3[CH:10]=[CH:9][CH:8]=2)(=[O:14])=[O:13])[CH2:18][CH2:17]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 66868231Tert-butyl 4-(isoquinolin-5-ylsulfonyl)-1,4-diazepane-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of isoquinoline-5-sulfonylchloride hydrochloride (3.00 g, 11.4 mmol) in anhydrous methylene chloride (100 mL) was added tert-butyl 1-homopiperazine carboxylate (3.00 g, 15.0 mmol) and triethylamine (4.36 g, 43.1 mmol). The mixture was stirred for 3 h, evaporated to dryness, mixed with a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (80 mL×2). The combined extracts were dried, filtered and evaporated to give an oil (4.45 g, 100%). LCMS (+APCI) m/z 392 (M+H).

Workup

  1. customevaporated to dryness
  2. additionmixed with a saturated solution of sodium bicarbonate (100 mL)
  3. extractionextracted with ethyl acetate (80 mL×2)
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f10ba3a512c34ebf9da25271aa1f2294
Source dataset
uspto-grants-2011_01
Patent number
US07867999B1

Reaction notes

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