4-Toluenesulfonyl chloride → HCID 58932564, compound

HRID 853894Notes

Reaction equation

HRID 853894 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:29][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([S:19]([N:22]4[CH2:26][CH2:25][CH2:24][C@H:23]4[CH2:27][OH:28])(=[O:21])=[O:20])=[CH:11][C:12]=3[C:13]3([O:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:5]2=[N:4][CH2:3]1.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.[Cl-].[Na+].O>[CH3:41][C:31]1[CH:36]=[CH:35][C:34]([S:37]([O:28][CH2:27][C@@H:23]2[CH2:24][CH2:25][CH2:26][N:22]2[S:19]([C:10]2[CH:9]=[CH:8][C:7]3[N:6]4[CH2:29][C:2]([CH3:30])([CH3:1])[CH2:3][N:4]=[C:5]4[C:13]4([O:18][CH2:17][CH2:16][CH2:15][O:14]4)[C:12]=3[CH:11]=2)(=[O:21])=[O:20])(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11553861HCID 11553861, compound

Product 1

HCID 58932564HCID 58932564, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of {(2S)-1-[(3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indol]-8′-yl)sulfonyl]pyrrolidin-2-yl}methanol (0.100 g, 2.300 mmol), p-toluenesulfonyl chloride (0.070 g, 0.340 mmol), N,N-diisopropylethylamine (0.100 ml, 0.580 mmol) and 4-(dimethylamino)pyridine (0.020 g, 0.070 mmol) in CH2Cl2 (5 mL) was stirred at rt for 2 days. The reaction was poured into brine and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound as a white foam (0.132 g, 97% ). Anal: Calc'd for C28H35N3O7S2: C, 57.03; H, 5.98; N, 7.13. Found: C, 56.38; H, 5.65; N, 6.81. NMR (400 Mz, DMSO-d6): consistent. MS: (ESI+) m/z 590.3 [M+H].

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2db4fc7157c44329bcd4a7447e1f1e7e
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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