1,3-Thiazole-2-carbaldehyde → Tert-butyl 3-(3-(thiazol-2-ylmethylamino)phenyl)propylcarbamate

HRID 1189975Notes

Reaction equation

HRID 1189975 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=2)CCCCC1.[S:26]1[CH:30]=[CH:29][N:28]=C1C=O.[BH4-].[Na+]>CO>[S:26]1[CH:30]=[CH:29][N:28]=[C:1]1[CH2:7][NH:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 27349031,3-Thiazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 59317002Tert-butyl 3-(3-(cyclohexylmethylamino)phenyl)propylcarbamate

Product 1

HCID 68524532Tert-butyl 3-(3-(thiazol-2-ylmethylamino)phenyl)propylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Å-3 Molecular sieves were added to a solution of aniline 17 (0.4 g, 1.6 mmol) and thiazole-2-carbaldehyde (0.18 g, 1.6 mmol) in MeOH. The reaction mixture was stirred for 18 h and then NaBH4 (0.121 g, 3.2 mmol) was added and the reaction mixture was stirred for overnight. The reaction mixture was filtered through Celite, concentrated under reduced pressure Purification by column chromatography (100-200 silica mesh, 20% EtOAc in hexane) gave tert-butyl 3-(3-(thiazol-2-ylmethylamino)phenyl)propylcarbamate as a brown oil. Yield (0.17 g, 31%); 1H NMR (400 MHz, DMSO-d6) δ 7.73 (d, J=3.2 Hz, 1H), 7.56 (d, J=3.2 Hz, 1H), 6.96 (t, J=7.6 Hz, 1H), 6.80 (bs, 1H), 6.45-6.38 (m, 4H), 4.55 (d, J=6.0 Hz, 2H), 2.91 (q, J=6.4 Hz, 2H), 2.39 (t, J=7.2 Hz, 2H), 1.59 (quintet, J=7.2 Hz, 2H), 1.37 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred for overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under reduced pressure Purification by column chromatography (100-200 silica mesh, 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-1d2be40211504394b511cd6b2895fe95
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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