Hydrochloric Acid → [(R)-3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-o-tolyl-methanone

HRID 598504

Reaction equation

HRID 598504 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][CH:10]3[CH2:14][CH2:13][NH:12][CH2:11]3)[O:8][C:4]=2[CH:3]=1.Cl.[CH3:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C@@H:10]3[CH2:14][CH2:13][N:12]([C:21]([C:20]4[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=4[CH3:18])=[O:22])[CH2:11]3)[O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 83732-Methylbenzoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57748894(6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amine

Product 1

HCID 57748968[(R)-3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-o-tolyl-methanoneYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 32.9 mg (0.12 mmol) (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amine; hydrochloride, 19.6 mg (0.144 mmol) 2-methyl-benzoic acid, 53.9 mg (0.168 mmol) TBTU and 77.5 mg (0.6 mmol) DIPEA in 2 mL DMF was stirred at room temperature for 16 h. The mixture was concentrated, taken up in methanol and formic acid and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 26.2 mg (61%) of the title compound. (MH+) 356.1.

Workup

  1. concentrationThe mixture was concentrated
  2. customformic acid and subjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-319c5c7a371c41038d972afcf6a6310f
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Linked notes

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