Sodium Hydroxide → HCID 58550626, compound

HRID 1890723Notes

Reaction equation

HRID 1890723 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[CH2:43][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:23][CH2:24][CH:25]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:26][NH:27][C:28]1([C:33]([O:35]C)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)=[CH:16]3.[OH-].[Na+]>CO>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:43][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:23][CH2:24][CH:25]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH2:26][NH:27][C:28]1([C:33]([OH:35])=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]1)=[CH:16]3

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 58550619HCID 58550619, compound

Product 1

HCID 58550626HCID 58550626, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of methyl 1-{[3-({[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-3-yl]methyl}amino)-2-phenylpropyl]amino}cyclopentanecarboxylate from Step E (0.136 g, 0.236 mmol) in methanol (2 mL) was added NaOH (0.472 mL, 1 M in water). The solution is then allowed to stir for 18 h at ambient temperature. Additional NaOH (0.472 mL, 1 M in water) was then added to the reaction, which was completed after another 24 h of stirring. The solution was then concentrated in vacuo and neutralized by addition of HCl (0.944 mL, 1 M in water). The resulting precipitate was filtered to yield the title compound. MS: m/z=562 (M+1).

Workup

  1. waitwas completed after another 24 h
  2. stirringof stirring
  3. concentrationThe solution was then concentrated in vacuo
  4. additionneutralized by addition of HCl (0.944 mL, 1 M in water)
  5. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-5c7005ed8b7a4e5496b0f590ad1b520e
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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