1H-imidazole-2-carbaldehyde → HCID 22256490, compound

HRID 351173Notes

Reaction equation

HRID 351173 reaction equation
[N+](C1C=CC=CC=1S([N:13]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH:23]2[CH2:32][C:31]3[N:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:25][CH2:24]2)=[CH:17][CH:16]=1)(=O)=O)([O-])=O.[NH:40]1[CH:44]=[CH:43][N:42]=[C:41]1[CH:45]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH2:45][C:41]2[NH:42][CH:43]=[CH:44][N:40]=2)[CH:23]2[CH2:32][C:31]3[N:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:25][CH2:24]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22708750HCID 22708750, compound

Product 1

HCID 22256490HCID 22256490, compoundYield 120.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using general procedure B: Reaction of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-7-quinolinyl)-1,4-benzenedimethanamine (175 mg, 0.32 mmol), imidazole-2-carboxaldehyde (155 mg, 1.6 mmol) and NaBH(OAc)3 (137 mg, 0.64 mmol) in MeOH (3 mL) for 8 hours at 60° C., followed by purification of the crude material by column chromatography on silica gel (CHCl3/MeOH/NH4OH 20:2:1) gave the desired product (169 mg, 84%) as a yellow/green foam.

Workup

  1. customfollowed by purification of the crude material by column chromatography on silica gel (CHCl3/MeOH/NH4OH 20:2:1)

Sources & evidence

ORD record
ord-cf46b7d62757449cb8a99b696a48b59c
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

Loading…