Hydrochloric Acid → HCID 19379103, compound

HRID 2210605Notes

Reaction equation

HRID 2210605 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.[OH-].[Li+].Cl>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53779467HCID 53779467, compound

Product 1

HCID 19379103HCID 19379103, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(pyridin-3-yl)-7-[1-(2-carboethoxyethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H--pyrrolo[1,2-c]thiazole (90 mg, 0.17 mmol), and lithium hydroxide (11 mg), where stirred in 33% aqueous THF (15 mL) for 45 min. The reaction mixture was diluted with H2O and taken to pH 4 with 1M aqueous HCl. The reaction mixture was extracted three times with ethyl acetate. The combined organic layers where dried over MgSO4, filtered,and concentrated in vacuo. 3-(Pyridin-3-yl)-7-[1-(2-carboxyethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (63 mg), was crystallized from ethyl acetate, hexanes. 1H NMR (CDCl3, 300MHz) δ2.95 (t, 2H, J=6, 7 Hz), 4.5-4.65 (m, 4H), 6.14 (d, 1H, J=3 Hz), 6.45 (s, 1H), 6.73 (d, 1H, J=3 Hz), 7.15 (t, 2H, J=9, 11Hz), 7.38-7.43 (m, 1H), 7.52 (d, 2H, J=8 Hz), 7.6-7.7 (m, 3H), 8.05 (s, 1H), 8.46 (d, 1H, J=9 Hz), 8.57 (bs, 2H), MS (DCI/NH3) m/e 512 (M+H)+. Anal calcd for C29H22N3O3SF; C, 68.09; H, 4.33; N, 8.21. Found: C, 67.78; H, 3.90; N, 8.06.

Workup

  1. extractionThe reaction mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers where dried over MgSO4
  3. concentrationfiltered,and concentrated in vacuo
  4. custom3-(Pyridin-3-yl)-7-[1-(2-carboxyethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (63 mg), was crystallized from ethyl acetate, hexanes

Sources & evidence

ORD record
ord-5aa0c7c913e444dc992e80212a3b8400
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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