Diisopropylethylamine → 4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-N-pyrrolidin-1-yl-benzamide

HRID 1783400ノート

反応式

HRID 1783400 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.CCN(C(C)C)C(C)C.Cl.[NH2:63][N:64]1[CH2:68][CH2:67][CH2:66][CH2:65]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:63][N:64]3[CH2:68][CH2:67][CH2:66][CH2:65]3)=[O:29])=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 686243374-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid

生成物 1

HCID 160354754-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-N-pyrrolidin-1-yl-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid (50 mg, 0.10 mmol) was dissolved in DMF (1 ml) and activated with the coupling reagent TPTU (33 mg, 0.11 mmol) and Hünig's base (0.03 ml, 0.26 mmol) for 2 min. 1-Aminopyrrolidine hydrochloride (0.013 g, 0.22 mmol) and further Hünig's base (0.03 ml, 0.26 mmol were added. After 1 h the reaction mixture was concentrated under reduced pressure and the residue taken up in ethyl acetate and washed with 5% KHSO4/10% K2SO4 (2×), water, brine, dried (MgSO4), filtered, concentrated under reduced pressure and purified over silica gel (ethyl acetate->ethyl acetate/5% MeOH) and the purified product was lyophilized: white lyophilisate 32 mg;

後処理

  1. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  2. washwashed with 5% KHSO4/10% K2SO4 (2×), water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified over silica gel (ethyl acetate->ethyl acetate/5% MeOH)

出典と根拠

ORDレコード
ord-903a00b6940a4f14a328e8c3828555f4
出典データセット
uspto-grants-2009_03
特許番号
US07501406B2

反応ノート

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