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

HRID 598504

反応式

HRID 598504 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-319c5c7a371c41038d972afcf6a6310f
出典データセット
uspto-grants-2011_03
特許番号
US07897627B2

関連ノート

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