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

HRID 598504

반응식

HRID 598504 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-319c5c7a371c41038d972afcf6a6310f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897627B2

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