Methanesulfonic Acid → HCID 11541071, compound

HRID 1695277Notes

Reaction equation

HRID 1695277 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:34])[C:13]2[O:19][C:18]3[C:20]([Cl:30])=[CH:21][C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:32])(=[O:31])[C:14]=2[CH:33]=1)=[O:9]>CO>[S:2]([OH:5])(=[O:4])(=[O:3])[CH3:1].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:34])[C:13]2[O:19][C:18]3[C:20]([Cl:30])=[CH:21][C:22]([N:24]4[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:31])(=[O:32])[C:14]=2[CH:33]=1)=[O:9]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 11541071HCID 11541071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methane sulfonic acid (0.023 mL, 0.3612 mmol) in methanol (1 mL) was added to a solution of 4-chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester (free base of example 16, 0.15 g, 0.344 mmol) in methanol (10 mL) at 25° C. and stirred for 15 min. The resultant precipitate was filtered, washed using methanol and dried to obtain the title compound. Yield: 0.13 g, (71%); mp 279-281° C.; 1H NMR (CDCl3, 300 MHz): δ 2.30 (s, 3H, CH3), 2.63 (s, 3H, CH3), 3.22 (s, 4H, 2CH2), 3.39 (s, 4H, 2CH2), 3.85 (s, 3H, OCH3), 5.17 (s, 2H, CH2), 7.18 (s, 1H, Ar), 7.20 (s, 1H, Ar), 8.09 (s, 1H, Ar), 8.15 (s, 1H, Ar), 8.72 (s, 2H, NH2); MS: m/e (ES+) 437 (M+1, free base); analysis: C21H25ClN2O8S2 requires C, 47.32,H, 4.73, N, 5.26, Cl, 6.65, S, 12.03; found: C, 47.80, H, 4.93, N, 5.44, Cl, 7.07, S, 11.75%.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-1aa5d67a8ef445efabfd64ab90c5fe86
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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