Tetrahydrofuran → HCID 11387774, compound

HRID 1431979Notes

Reaction equation

HRID 1431979 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:16]=[C:15]([CH:17]=O)[CH:14]=[C:13]2[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1COCC1.[O:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=2)[CH2:38][CH2:37]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH:16]=[C:15]([CH2:17][NH:46][C:45]3[CH:47]=[CH:48][C:42]([N:39]4[CH2:38][CH2:37][O:36][CH2:41][CH2:40]4)=[CH:43][CH:44]=3)[CH:14]=[C:13]2[C:19]2[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 5049666Sodium triacetoxyborohydrideHCID 87516624HCID 87516624, compound

Product 1

HCID 11387774HCID 11387774, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of 1-p-methoxyphenylsulfonyl-2-(3,4,5-trimethoxyphenyl)pyrrole-4-carbaldehyde (50 mg, 0.12 mmol, Example 94a) in THF (1 ml) acetic acid (21 mg, 3 equiv.), 4-morpholinoaniline (21 mg, 1.05 equiv.) and NaBH(OAc)3 (61 mg, 2.5 equiv.) are added. The reaction mixture is stirred at room temperature for 16 h, and diluted with aqueous 1 M Na2CO3 solution and ethyl acetate. The organic layer is dried (MgSO4) and purified by flash chromatography and preparative HPLC. RT (program 2) 3.52. MS: 593.7.

Workup

  1. dry with materialThe organic layer is dried (MgSO4)
  2. custompurified by flash chromatography and preparative HPLC
  3. customRT (program 2) 3.52

Sources & evidence

ORD record
ord-575846743196406aa24248610b40e52d
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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