Hydrochloric Acid → HCID 67232788, compound

HRID 733111Notes

Reaction equation

HRID 733111 reaction equation
[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23]3)[CH2:17][CH2:16]2)=[O:12])[C:3]1=[O:29].[ClH:31]>O1CCCC1>[ClH:31].[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23]3)[CH2:17][CH2:16]2)=[O:12])[C:3]1=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11611338HCID 11611338, compound

Product 1

HCID 67232788HCID 67232788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

1-{[4-({[(3,3-Dimethyl-2-oxo-2,3-dihydro-1h-indol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclobutanecarboxylic acid (41.0 g, 99.2 mmol, Example 9) was dissolved with tetrahydrofuran (820 mL). The mixture was filtered and washed with tetrahydrofuran (410 mL) and the resulting solution was heated to 45° C. Aqueous concentrated hydrogen chloride (12N, 8.27 mL, 99.2 mmol) was added to the solution at 45° C. for 20 min and stirred at this temperature for 1 h. The suspension was cooled to 20° C. for 1 min stirred at 2 h. After filtration, the resulting solid was washed with tetrahydrofuran (205 mL), and dried in vacuo at 40° C. The titled compound was obtained as white solid (38.6 g, 86.6%)

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with tetrahydrofuran (410 mL)
  3. temperatureThe suspension was cooled to 20° C. for 1 min
  4. stirringstirred at 2 h
  5. filtrationAfter filtration
  6. washthe resulting solid was washed with tetrahydrofuran (205 mL)
  7. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-a3ad91ba5be84d86a5e42aca7b5db3ba
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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