Hydrochloric Acid → (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-cyclopentylbenzo[d]thiazole-6-carboxamide

HRID 447161Notes

Reaction equation

HRID 447161 reaction equation
C(OC([NH:8][C@@H:9]([CH2:30][C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27](O)=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.[CH:36]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37]1.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.Cl>CN(C=O)C.C(OCC)(=O)C.O1CCOCC1>[NH2:8][C@@H:9]([CH2:30][C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([NH:41][CH:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67236426(S)-2-(4-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

Product 1

HCID 58318229(S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-cyclopentylbenzo[d]thiazole-6-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

(S)-2-(4-(2-(tert-Butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (0.084 g, 0.155 mmol), cyclopentylamine (0.015 ml, 0.155 mmol), diisopropylethylamine (0.11 ml, 0.62 mmol) and HBTU (0.076 g, 0.20 mmol) were dissolved in DMF (4 ml) and the resulting mixture stirred overnight. The resulting mixture was then diluted with ethyl acetate (9 ml), washed with 1N HCl (3×5 ml), brine (5 ml), dried (MgSO4) and concentrated in vacuo. The resulting residue was chromatographed eluting with dichloromethane/methanol (97:2) to yield a residue which was dissolved in 1,4-dioxane (1 ml) and treated with 4M HCl in 1,4-dioxane for three days. The resulting solid was filtered, washed with ether (3×) and dried to yield (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-cyclopentylbenzo[d]thiazole-6-carboxamide (Compound #26).

Workup

  1. washwashed with 1N HCl (3×5 ml), brine (5 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was chromatographed
  5. washeluting with dichloromethane/methanol (97:2)
  6. customto yield a residue which
  7. filtrationThe resulting solid was filtered
  8. washwashed with ether (3×)
  9. customdried

Sources & evidence

ORD record
ord-ec5cbf88f406441ba366e48d1a0c1ff6
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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