Pyrrolidine → HCID 23728896, compound

HRID 1944691Notes

Reaction equation

HRID 1944691 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C1COCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:21])=[CH:15][C:13]=3[N:14]=2)[CH2:8][CH2:9]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59588797HCID 59588797, compound

Product 1

HCID 23728896HCID 23728896, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-5-carboxylic acid (530 mg, 1.75 mmol), pyrrolidine (149 mg, 2.10 mmol) and DIEA in THF (7.3 mL) was stirred for 30 min at rt. Then PyBOP was added and the reaction mixture was stirred at rt overnight. The mixture was concentrated and the residue was neutralized with an aqueous solution of Na2CO3 to pH 7. Then the mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified with preparative HPLC to give 490 mg (78%) of (2-(4-isopropylpiperazin-1-yl)benzothiazol-5-yl)(pyrrolidin-1-yl)methanone as a trifluoroacetate salt.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThen the mixture was extracted with dichloromethane (3×10 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified with preparative HPLC

Sources & evidence

ORD record
ord-4737c9e152654941a5b1e30fc43affd2
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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