Diisopropylethylamine → HCID 67236274, compound

HRID 447159Notes

Reaction equation

HRID 447159 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:20][C:21]([O:24][C:25]([NH:27][C@H:28]([C:35](O)=[O:36])[CH2:29][C:30]1[S:34][CH:33]=[CH:32][CH:31]=1)=[O:26])([CH3:23])[CH3:22].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>[C:21]([O:24][C:25]([NH:27][C@@H:28]([CH2:29][C:30]1[S:34][CH:33]=[CH:32][CH:31]=1)[C:35]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2][CH2:3]1)=[O:36])=[O:26])([CH3:23])([CH3:20])[CH3:22]

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 67236548HCID 67236548, compound

Product 1

HCID 67236274HCID 67236274, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(piperazin-1-yl)benzo[d]thiazole-6-carboxylate (0.35 g, 1.26 mmol), Boc-L-2-thienylalanine (0.34 g, 1.26 mmol), diisopropylethylamine (0.88 ml, 5.06 mmol) and HBTU (0.62 g, 1.64 mmol) were dissolved in DMF (36 ml) and the resulting mixture stirred overnight. The resulting mixture was then diluted with ethyl acetate (78 ml), washed with 1N HCl (3×39 ml), washed with brine (39 ml), dried (MgSO4) and concentrated in vacuo. The resulting residue was chromatographed eluting with dichloromethane/methanol (97:3) to yield (S)-methyl 2-(4-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylate.

Workup

  1. washwashed with 1N HCl (3×39 ml)
  2. washwashed with brine (39 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-0ee29dfc8bfe46fbadfccb534a188038
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

Loading…