Acetic Acid → HCID 58550619、化合物

HRID 1890722ノート

反応式

HRID 1890722 の反応式
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:24][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH:22]=O)=[CH:16]3.CC(O)=O.Cl.Cl.[NH2:31][CH2:32][CH:33]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:34][NH:35][C:36]1([C:41]([O:43][CH3:44])=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:24][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH2:22][NH:31][CH2:32][CH:33]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:34][NH:35][C:36]1([C:41]([O:43][CH3:44])=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37]1)=[CH:16]3

参加物

9

反応物 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59594304HCID 59594304、化合物2 回HCID 67211652HCID 67211652、化合物

生成物 1

HCID 58550619HCID 58550619、化合物

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒2 回HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a stirred suspension of 2′-oxo-1′,2′, 6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (80.0 mg, 0.254 mmol, Intermediate 1) and HOAc (31 μL, 0.533 mmol) in dry chloroform (3 mL) was added a solution of methyl 1-[(3-amino-2-phenylpropyl)amino]cyclopentanecarboxylate dihydrochloride from Step D (106 mg, 0.304 mmol) and Hunig's base (106 μL, 0.609 mmol) in dry chloroform (2 mL). After 15 minutes, sodium triacetoxyborohydride (108 mg, 0.507 mmol) was added. After 4 hours of stirring, the mixture was diluted with DCM and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted once with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue. The residue was then was applied to a silica gel column for purification, eluting with a gradient of DCM:MeOH (with 10% NH4OH)—99:1 to 86:14 to give the title compound. MS: m/z=576 (M+1).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once with DCM
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue
  7. customThe residue was then was applied to a silica gel column for purification
  8. washeluting with a gradient of DCM

出典と根拠

ORDレコード
ord-fe4fb27041fd47d3b9b5f966e0f5fb15
出典データセット
uspto-grants-2013_08
特許番号
US08507477B2

反応ノート

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