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Formic Acid → {(S)-3-[(6-Chloro-benzooxazol-2-ylamino)-methyl]-pyrrolidin-1-yl}-(2,6-dimethoxy-phenyl)-methanone

HRID 222417
ノート
印刷プレビュー

反応式

HRID 222417 の反応式
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([NH:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][NH:14][CH2:13]3)[O:9][C:5]=2[CH:4]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=1[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(O)=O>CN(C=O)C.CCN(C(C)C)C(C)C>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([NH:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][N:14]([C:23]([C:22]4[C:26]([O:30][CH3:31])=[CH:27][CH:28]=[CH:29][C:21]=4[O:20][CH3:19])=[O:24])[CH2:13]3)[O:9][C:5]=2[CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 284Formic AcidHCID 151092,6-Dimethoxybenzoic AcidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131728778(6-Chloro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride2 回

生成物 1

HCID 44628353{(S)-3-[(6-Chloro-benzooxazol-2-ylamino)-methyl]-pyrrolidin-1-yl}-(2,6-dimethoxy-phenyl)-methanone
収率 38.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

A mixture of 146.3 mg (0.45 mmol) (6-chloro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride (intermediate 1), 106.7 mg (0.586 mmol) 2,6-dimethoxy-benzoic acid (commercially available) and 206.9 mg (0.64 mmol) TBTU in 4 mL DMF and 0.3 mL DIPEA was shaken at room temperature over night. The mixture was acidified with 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 72 mg (38%) of the title compound. MS (m/e): 416.2 (MH+).

後処理

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

出典と根拠

ORDレコード
ord-50e5193ec4c644509b3b0a3bc1e135c5
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08207220B2

反応ノート

読み込み中…

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