Trifluoroacetic acid → HCID 86687522, compound

HRID 1473473Notes

Reaction equation

HRID 1473473 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:29]1[S:30][CH:31]=[CH:32][N:33]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([CH:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH2:25][CH2:26][O:27][CH3:28])=[N:15][CH:14]=[CH:13]2)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:28][O:27][CH2:26][CH2:25][N:21]1[CH2:22][CH2:23][CH2:24][CH:20]1[C:16]1[C:17]2[C:12](=[CH:11][C:10]([S:7]([NH:6][C:29]3[S:30][CH:31]=[CH:32][N:33]=3)(=[O:8])=[O:9])=[CH:19][CH:18]=2)[CH:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687521HCID 86687521, compound

Product 1

HCID 86687522HCID 86687522, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-dimethoxybenzyl)-1-(1-(2-methoxyethyl)pyrrolidin-2-yl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (0.046 g, 0.080 mmol) was dissolved in DCM and TFA (0.1 ml, 1.298 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The reaction was concentrated, dissolved in methanol, and passed through an SCX ion exchange column (pre-wetted with methanol). The column was washed twice with methanol, then the product was liberated by flushing the column several times with a 2.0M ammonia/methanol solution. The product-containing solution was concentrated to afford 1-(1-(2-methoxyethyl)pyrrolidin-2-yl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm=8.79 (br. s., 1H), 8.53 (d, J=5.7 Hz, 1H), 8.46 (s, 1H), 8.00 (d, J=5.9 Hz, 1H), 7.93 (d, J=9.0 Hz, 1H), 7.17 (d, J=4.2 Hz, 1H), 6.74 (d, J=4.3 Hz, 1H), 4.60 (br. s., 1H), 3.55 (br. s., 2H), 2.96 (s, 3H), 2.82 (br. s., 1H), 2.71 (br. s., 2H), 2.42 (br. s., 1H), 2.00 (d, J=11.6 Hz, 2H), 1.95 (d, J=12.8 Hz, 1H). m/z (ESI) 419.1 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in methanol
  3. washThe column was washed twice with methanol
  4. customby flushing the column several times with a 2.0M ammonia/methanol solution
  5. concentrationThe product-containing solution was concentrated

Sources & evidence

ORD record
ord-3577f29d89cb4eb6813e85024863e320
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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