Acetic Acid → HCID 58550619, compound

HRID 1890722Notes

Reaction equation

HRID 1890722 reaction equation
[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

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59594304HCID 59594304, compound2×HCID 67211652HCID 67211652, compound

Product 1

HCID 58550619HCID 58550619, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fe4fb27041fd47d3b9b5f966e0f5fb15
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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