Cyclopentylamine → HCID 67236358, compound

HRID 447167Notes

Reaction equation

HRID 447167 reaction equation
[CH:1]([C:3]1[CH:34]=[CH:33][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16](=[O:32])[C@@H:17]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:18][C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1)=O.[CH:35]1([NH2:40])[CH2:39][CH2:38][CH2:37][CH2:36]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:35]1([NH:40][CH2:1][C:3]2[CH:34]=[CH:33][C:6]3[N:7]=[C:8]([N:10]4[CH2:11][CH2:12][N:13]([C:16](=[O:32])[C@@H:17]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:18][C:19]5[S:20][CH:21]=[CH:22][CH:23]=5)[CH2:14][CH2:15]4)[S:9][C:5]=3[CH:4]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86654770HCID 86654770, compound

Product 1

HCID 67236358HCID 67236358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 1-(4-(6-formylbenzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (45 mg), cyclopentylamine (12 mg), and sodium triacetoxyborohydride (29 mg) were combined in DCM (1 mL), and the resulting mixture stirred at room temperature overnight, then heated to reflux for 24 hours. The resulting mixture was then cooled to room temperature, quenched with saturated aqueous sodium bicarbonate, extracted with DCM, and chromatographed (0 to 5% MeOH in DCM) to yield (S)-tert-butyl 1-(4-(6-((cyclopentylamino)methyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperatureThe resulting mixture was then cooled to room temperature
  4. customquenched with saturated aqueous sodium bicarbonate
  5. extractionextracted with DCM
  6. customchromatographed (0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-4e6e1c40898b467ca65dacf61356b8f2
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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