Diisopropylethylamine → HCID 67345592, compound

HRID 1257654Notes

Reaction equation

HRID 1257654 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18](Cl)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([N:30]1[CH2:34][CH2:33][C@@H:32]([NH2:35])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH2:23]([N:30]1[CH2:34][CH2:33][C@@H:32]([NH:35][C:18]2[C:13]3[CH:12]=[CH:11][N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[C:14]=3[N:15]=[CH:16][C:17]=2[N+:20]([O-:22])=[O:21])[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 583947741-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 67345592HCID 67345592, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (2 g, 5.9 mmol), (R)-1-Benzyl-pyrrolidin-3-ylamine (2.4 g, 15.3 mmol), and diisopropylethylamine (6 mL, 35.4 mmol) in propan-2-ol (50 mL) was heated to reflux for 4 hours. Volatile components were removed under vacuum and the residue was purified by column chromatography on silica gel (gradient: 0 to 5% methanol in dichloromethane), gave 2.48 g (88%) of (R)—N-(1-benzylpyrrolidin-3-yl)-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine. LCMS (Method J, ESI): RT=0.98 min, M+H+=478.1; 1H NMR (400 MHz, CDCl3) δ: 9.29-9.27 (s, 1H), 9.10 (s, 1H), 8.20-8.17 (m, 2H), 7.63-7.57 (m, 2H), 7.53-7.49 (m, 2H), 7.36-7.25 (m, 6H), 6.77-6.76 (d, J=4.4, 1H), 4.55-4.54 (m, 1H), 3.73-3.63 (m, 1H), 2.94-2.91 (m, 1H), 2.78-2.77 (m, 2H), 2.49-2.41 (m, 4H), 1.90-1.88 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customVolatile components were removed under vacuum
  4. customthe residue was purified by column chromatography on silica gel (gradient: 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-843bb02f88404a659a59d5d9cf319eb0
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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