Hydrochloric Acid → HCID 11659330, compound

HRID 1435926Notes

Reaction equation

HRID 1435926 reaction equation
[O:1]=[C:2]1[C@@H:11]2[CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][C@H:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:22]([F:25])([F:24])[F:23])[C:4]=2[NH:3]1.[ClH:26]>CCOCC>[ClH:26].[F:25][C:22]([F:23])([F:24])[C:5]1[C:4]2[NH:3][C:2](=[O:1])[C@@H:11]3[CH2:12][NH:13][CH2:14][C@H:10]3[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69056746HCID 69056746, compound2×

Product 1

HCID 11659330HCID 11659330, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the second eluting compound from Example 7, Part B, tentatively assigned as (3aS,9bR)-tert-butyl 4-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate (50 mg, 0.14 mmol) in 4 mL of ether was added 1 mL of 12 N HCl. The resulting mixture was stirred at ambient temperature for 15 min and then was concentrated and dried in vacuo to a solid. This solid was triturated twice with ether and dried in vacuo to afford 35 mg (85%) of the title compound of Example 8 as a white solid. 1H NMR (DMSO-D6): δ 9.73 (s, 1H), 9.66 (broad s, 1H), 9.54 (broad s, 1H), 7.62 (d, 1H), 7.50 (d, 1H), 7.25 (t, 1H), 3.96-3.90 (m, 1H), 3.55-3.42 (overlapping m, 2H), 3.32-3.22 (overlapping m, 2H), 3.10-3.00 (m, 1H). LRMS (ESI): 257.2 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customdried in vacuo to a solid
  3. customThis solid was triturated twice with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4a8974abb2244566a654d86cba75a242
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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