Hydrochloric Acid → HCID 22311998, compound

HRID 497376Notes

Reaction equation

HRID 497376 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][N:24]2[C:32]3[CH2:31][CH2:30][N:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:28][C:27]=3[C:26]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)=[N:25]2)[CH2:17][CH2:16]1)=[O:4].[OH-].[K+].Cl>C1COCC1.O>[F:14][C:11]1[CH:12]=[CH:13][C:7]2[C:6]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][N:24]4[C:32]5[CH2:31][CH2:30][N:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:28][C:27]=5[C:26]([C:37]5[CH:42]=[CH:41][C:40]([C:43]([F:45])([F:46])[F:44])=[CH:39][CH:38]=5)=[N:25]4)[CH2:19][CH2:20]3)=[C:5]([C:3]([OH:4])=[O:2])[S:9][C:8]=2[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 44433598HCID 44433598, compound

Product 1

HCID 22311998HCID 22311998, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 635 mg (0.94 mmol) of 6-fluoro-3-(1-{3-[5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propyl}-piperidin-4-yl)-benzo[b]thiophene-2-carboxylic acid methyl ester in 10 mL of THF was treated a solution of 53 mg (0.94 mmol) of KOH in 0.5 mL of water. This was stirred overnight, after the hydrolysis was deemed complete 1 mL of 1 N HCl solution was added. This was then extracted with EtOAc (3×30 mL). The combined organic layers were then washed with brine, dried over Na2SO4, and concentrated to yield 622 mg (100%) of a white solid. MS (electrospray): exact mass calculated for C31H32F4N4O4S2: 664.18; m/z found, 665.2 [M+H]+. 1H NMR (DMSO-d6, 400 MHz): 8.12 (dd, J=8.81, 5.28 Hz, 1H), 7.83 and 7.76 (A and B of AB quartet, J=8.41 Hz, 4H), 7.17 (br t, J=8.61 Hz, 1H), 4.47 (s, 2H), 4.29 (br s, 1H), 4.16 (t, J=7.04 Hz, 2H), 3.53 (t, J=5.67 Hz, 2H), 3.28 (br m, 4H), 3.00 (s, 3H), 2.96 (m, 2H), 2.73 (br s, 2H), 2.52 (br m, 2H), 2.13 (br m, 2H), 1.76 (br m, 2H).

Workup

  1. additionwas added
  2. extractionThis was then extracted with EtOAc (3×30 mL)
  3. washThe combined organic layers were then washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b91bef6bca5f43aa858dc514d2bbe500
Source dataset
uspto-grants-2005_09
Patent number
US06949540B2

Reaction notes

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