Diisopropylethylamine → (S)-tert-butyl 1-(4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

HRID 447155Notes

Reaction equation

HRID 447155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:28]=[CH:27][C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[S:20][C:16]=3[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:29][C:30]([O:33][C:34]([NH:36][C@H:37]([C:44](O)=[O:45])[CH2:38][C:39]1[S:43][CH:42]=[CH:41][CH:40]=1)=[O:35])([CH3:32])[CH3:31].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:28]=[CH:27][C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][N:24]([C:44](=[O:45])[C@@H:37]([NH:36][C:34](=[O:35])[O:33][C:30]([CH3:29])([CH3:31])[CH3:32])[CH2:38][C:39]5[S:43][CH:42]=[CH:41][CH:40]=5)[CH2:23][CH2:22]4)[S:20][C:16]=3[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27344843-(Thien-2-yl)-L-alanine, N-BOC protectedHCID 67236491N-(3,4-dimethoxyphenyl)-2-(piperazin-1-yl)benzo[d]thiazole-6-carboxamide

Product 1

HCID 67235777(S)-tert-butyl 1-(4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3,4-dimethoxyphenyl)-2-(piperazin-1-yl)benzo[d]thiazole-6-carboxamide (1.00 g, 2.51 mmol), Boc-L-2-thienylalanine (0.68 g, 2.551 mmol), diisopropylethylamine (1.75 ml, 10.04 mmol) and HBTU (1.24 g, 3.26 mmol) were dissolved in DMF (71 ml) and stirred overnight. The resulting mixture was diluted with ethyl acetate (154 ml), washed with 1N HCl (3×77 ml), washed with brine (77 ml), dried (MgSO4) and concentrated in vacuo. The resulting residue was chromatographed, eluting with dichloromethane/methanol (97:3) to yield (S)-tert-butyl 1-(4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate.

Workup

  1. washwashed with 1N HCl (3×77 ml)
  2. washwashed with brine (77 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed
  6. washeluting with dichloromethane/methanol (97:3)

Sources & evidence

ORD record
ord-422c8e2639e84e5394e6c7f7bb5b66e8
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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