Diisopropylethylamine → (1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-amine

HRID 1257751Notes

Reaction equation

HRID 1257751 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.[N:23]1[C:27]2[CH2:28][CH2:29][CH:30]([NH2:32])[CH2:31][C:26]=2[NH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(O)C>[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]([NH:32][CH:30]4[CH2:29][CH2:28][C:27]5[N:23]=[CH:24][NH:25][C:26]=5[CH2:31]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1559244,5,6,7-tetrahydro-1H-1,3-benzodiazol-5-amineHCID 583947741-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 67345609(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-amineYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (1 g, 3 mmol) and 4,5,6,7-Tetrahydro-3H-benzoimidazol-5-ylamine (450 mg, 3.3 mmol) in ethanol (50 ml) was added DIPEA (1 ml, 9.9 mmol). The mixture was heated to reflux for 1 h. Volatile components were removed, and the residue was extracted with ethyl acetate, washed with water and brine, the organic layer was purified by column chromatography (eluting with 10˜20% methanol in dichloromethane) to give 0.75 g (57%) of (1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4,5,6,7-tetrahydro-3H-benzoimidazol-5-yl)-amine. LCMS (Method J, ESI): RT=0.95, m+H=438.9; 1H NMR (400 MHz, CDCl3+2 drops of CD3OD) δ: 9.20-9.15 (m, 1H), 9.05 (s, 1H), 8.17-8.14 (m, 2H), 8.05-8.00 (s, 1H), 7.65-7.48 (m, 2H), 7.55-7.45 (m, 2H), 6.80-6.75 (m, 1H), 4.60-4.50 (m, 1H), 3.30-3.20 (m, 1H), 2.95-2.80 (m, 3H), 2.30-2.00 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customVolatile components were removed
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with water and brine
  6. customthe organic layer was purified by column chromatography (eluting with 10˜20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6c533e672519461580ccef225cac8cf1
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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