Dimethylformamide → 2-(cyclohexylmethyl)-N-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide monofumarate

HRID 1182987Notes

Reaction equation

HRID 1182987 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH:9]1([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([S:26]([NH:29][CH2:30][CH2:31][C@@H:32]4[CH2:36][CH2:35][CH2:34][N:33]4[CH3:37])(=[O:28])=[O:27])=[CH:21][CH:22]=3)[CH2:17]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CN(C=O)C.C(OC(C)C)(=O)C>O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH:9]1([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([S:26]([NH:29][CH2:30][CH2:31][C@@H:32]4[CH2:36][CH2:35][CH2:34][N:33]4[CH3:37])(=[O:27])=[O:28])=[CH:21][CH:22]=3)[CH2:17]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7915Isopropyl AcetateHCID 444972Fumaric AcidHCID 115026452-(cyclohexylmethyl)-N-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide

Product 1

HCID 498538442-(cyclohexylmethyl)-N-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide monofumarate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fumaric acid (1.86 g, 16 mmol) was added to 2-(cyclohexylmethyl)-N-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide (6.7 g, 16 mmol). DMF (10 mL) and water (500 μL) were added to the mixture, and the solids were dissolved by warming on a steam bath. Isopropyl acetate (30 mL) was added gradually while heating on a steam bath. The heat was removed, and material oiled out. The mother liquors were decanted. About 100 mL MTBE were added to the residual oil, which was stirred for several hours until the mixture was a uniform slurry. A solid was collected and washed with MTBE. The solid was harvested and dried by vacuum filtration on a Büchner funnel. NMR shows a 1.9:1 ratio of fumaric acid to base. The solid was air-dried over night.

Workup

  1. dissolutionthe solids were dissolved
  2. temperatureby warming on a steam bath
  3. temperaturewhile heating on a steam bath
  4. customThe heat was removed
  5. customThe mother liquors were decanted
  6. additionAbout 100 mL MTBE were added to the residual oil, which
  7. customA solid was collected
  8. washwashed with MTBE
  9. customdried by vacuum filtration on a Büchner funnel
  10. customThe solid was air-dried over night

Sources & evidence

ORD record
ord-4b29117d9e4c4c66b73b7095bd1ee043
Source dataset
uspto-grants-2014_03
Patent number
US08664245B2

Reaction notes

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