Triethylamine → HCID 44177821、化合物

HRID 1042531ノート

反応式

HRID 1042531 の反応式
[C:1]([C:3]1[CH:41]=[CH:40][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:23]4[NH:22][C:21]5[CH2:26][CH2:27][N:28](C(OCC6C=CC=CC=6)=O)[CH2:29][C:20]=5[C:19]=4[CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].Br.CC(O)=O.C(N(CC)CC)C.[F:54][C:55]([F:67])([F:66])[C:56]1[CH:61]=[CH:60][C:59]([S:62](Cl)(=[O:64])=[O:63])=[CH:58][CH:57]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:23]4[NH:22][C:21]5[CH2:26][CH2:27][N:28]([S:62]([C:59]6[CH:58]=[CH:57][C:56]([C:55]([F:54])([F:66])[F:67])=[CH:61][CH:60]=6)(=[O:64])=[O:63])[CH2:29][C:20]=5[C:19]=4[CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:40][CH:41]=1)#[N:2]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 44177300HCID 44177300、化合物

生成物 1

HCID 44177821HCID 44177821、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of benzyl 8-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (4a, 50 mg, 91 μmol) in DCM (dichloromethane) (1.0 mL) was added dropwise a solution of HBr/AcOH (48% w/v, 1.0 mL). After the resulting brown reaction mixture was stirred for 30 min, the volatiles were evaporated, MeOH (2 mL) was added and the volatiles evaporated again. The resulting brown residue was dissolved in DMF (1.0 mL) and triethylamine (0.5 mL, 0.36 g, 3.6 mmol) and 4-(trifluoromethyl)benzenesulfonyl chloride (45 mg, 0.2 mmol) were added. The resulting reaction mixture was allowed to stir at room temperature overnight, then poured into saturated sodium bicarbonate solution (20 mL) to give a brown precipitate which was filtered and purified by reverse phase HPLC to provide Compound 24 upon trituration with ethyl ether (18 mg, 31%). 1H NMR (DMSO-d6, 300 MHZ) 11.21 (br s, 1H), 11.18 (br s, 1H), 9.75 (br s, 1H), 8.26 (d, J=7.2 Hz, 1H), 8.07 (d, J=8.3 Hz, 2H), 7.98 (d, J=7.7 Hz, 4H), 7.71 (d, J=8.3 Hz, 2H), 7.57 (d, J=8.5 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 4.40 (d, J=8.3 Hz, 4H), 3.55-3.06 (m, 7H), 2.92-2.82 (m, 2H), 2.07 (d, J=10.5 Hz, 2H), 1.78 (q, J=11.3 Hz, 2H) ppm; MS (ES) 622 (M+H).

後処理

  1. customthe volatiles were evaporated
  2. additionMeOH (2 mL) was added
  3. customthe volatiles evaporated again
  4. dissolutionThe resulting brown residue was dissolved in DMF (1.0 mL)
  5. customThe resulting reaction mixture
  6. stirringto stir at room temperature overnight
  7. customto give a brown precipitate which
  8. filtrationwas filtered
  9. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-50cdfb6900df4b3084643e13aa464410
出典データセット
uspto-grants-2013_10
特許番号
US08557822B2

反応ノート

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