1H-imidazole-2-carbaldehyde → HCID 22018659, compound

HRID 351174Notes

Reaction equation

HRID 351174 reaction equation
[N+](C1C=CC=CC=1S([N:13]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:33][CH2:34][NH2:35])[CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1)(=O)=O)([O-])=O.[NH:43]1[CH:47]=[CH:46][N:45]=[C:44]1[CH:48]=O.[BH4-].[Na+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>CO>[N:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH2:33][CH2:34][NH:35][CH2:48][C:44]2[NH:45][CH:46]=[CH:47][N:43]=2)[CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 249551H-imidazole-2-carbaldehydeHCID 90495Di-tert-butyl dicarbonateHCID 4311764Sodium borohydrideHCID 22708779HCID 22708779, compound

Product 1

HCID 22018659HCID 22018659, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(2-aminoethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (333 mg, 0.57 mmol) in dry MeOH (5 mL) was added 2-imidazolecarboxaldehyde (110 mg, 1.14 mmol) and the mixture was stirred for 17 hours. To this solution was added sodium borohydride (110 mg, 2.91 mmol) in one portion and the mixture was stirred for 40 min. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (25 mL). The aqueous layer was washed with CH2Cl2 (2×20 mL) and the combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The crude amine was dissolved in THF (10 mL) and protected with di-t-butyldicarbonate (1.0 g, 4.59 mmol). Purification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH, 96:4 followed by 9:1) gave the desired product (110 mg, 22%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred for 40 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (25 mL)
  4. washThe aqueous layer was washed with CH2Cl2 (2×20 mL)
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe crude amine was dissolved in THF (10 mL)
  9. customPurification of the crude material by column chromatography on silica gel (CH2Cl2/MeOH, 96:4 followed by 9:1)

Sources & evidence

ORD record
ord-906e0321154b4113a83e091a5c7e3860
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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