Water → HCID 90412270, compound

HRID 1522031Notes

Reaction equation

HRID 1522031 reaction equation
[F:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH:13]4[CH2:17][NH:16][CH2:15][CH:14]4[CH:18]=3)[NH:8][C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].O>CN1CCCC1=O>[F:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH:13]4[CH2:17][N:16]([S:36]([CH3:35])(=[O:38])=[O:37])[CH2:15][CH:14]4[CH:18]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90413493HCID 90413493, compound

Product 1

HCID 90412270HCID 90412270, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of Example 282A in 1-methyl-2-pyrrolidinone (2 mL) was added triethylamine (0.177 mL, 1.267 mmol) and methanesulfonyl chloride (0.033 mL, 0.422 mmol) and the mixture was stirred for 3 hours. The mixture was treated with water and stirred for 10 minutes and the precipitate was filtered, washed with water, and vacuum oven-dried. The solid was suspended in 1 mL methanol and treated with 1 mL 2M hydrogen chloride in ether. The suspension was diluted with 4 mL ether, stirred for 10 minutes, filtered, washed with ether, and vacuum oven-dried to give the title compound as a hydrochloride salt. 1H NMR (400 MHz, Methanol-d4) δ 2.63-2.76 (m, 1H), 2.85 (s, 3H), 3.00-3.13 (m, 1H), 3.11-3.24 (m, 2H), 3.37-3.54 (m, 3H), 3.68-3.77 (m, 1H), 3.80 (s, 3H), 6.39-6.48 (m, 2H), 7.20-7.29 (m, 2H), 7.28-7.37 (m, 1H), 8.43 (d, J=3.9 Hz, 1H). MS (ESI+) m/z 446.2 (M+H)+.

Workup

  1. stirringstirred for 10 minutes
  2. filtrationthe precipitate was filtered
  3. washwashed with water, and vacuum
  4. customoven-dried
  5. additiontreated with 1 mL 2M hydrogen chloride in ether
  6. additionThe suspension was diluted with 4 mL ether
  7. stirringstirred for 10 minutes
  8. filtrationfiltered
  9. washwashed with ether, and vacuum
  10. customoven-dried

Sources & evidence

ORD record
ord-1a8c2acba13a42b3a6a644260c64ed16
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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