Methanesulfonic Acid → HCID 86621141, compound

HRID 1360335Notes

Reaction equation

HRID 1360335 reaction equation
[CH3:1][N:2]([CH3:29])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[O:15][C:16](=[O:28])[C:17]4[C:23]([CH2:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:18]=4[N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1.[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(OCC)C>[OH2:15].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[CH3:29][N:2]([CH3:1])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[O:15][C:16](=[O:28])[C:17]4[C:23]([CH2:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:18]=4[N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 25205741AX-9657

Product 1

HCID 86621141HCID 86621141, compoundYield 182.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of compound 132 (120 mg, 0.304 mmol) in diethyl ether (3.0 mL) was added methanesulfonic acid (0.0394 mL, 0.608 mmol) in diethyl ether (1.0 mL) at room temperature. After stirring for 30 min, the resulting solid was filtered, washed with diethyl ether, and dried in vacuo at room temperature, to give 2-[2-((S)-3-Dimethylamino-pyrrolidin-1-yl)-pyridin-3-yl]-5-ethyl-7-methoxy-4H-benz[d][1,3]oxazin-4-one methanesulfonate monohydrate (141 mg) as a white solid. Mp 43-49° C. [α]D25-205 (c 0.34, MeOH). 1H NMR (DMSO-d6, 400 MHz): δ 1.21 (3H, t, J=7.3 Hz), 2.07-2.12 (1H, m), 2.31-2.35 (1H, m), 2.33 (6H, s), 2.79 (3H, d, J=4.9 Hz), 2.82 (3H, d, J=4.3 Hz), 3.07-3.15 (2H, m), 3.48 (2H, dd, J=8.6, 5.5 Hz), 3.68-3.80 (2H, m), 3.89-3.96 (1H, m), 3.91 (3H, s), 6.27 (1H, brs), 6.91 (1H, dd, J=7.9, 4.9 Hz), 7.01 (1H, d, J=2.4 Hz), 7.03 (1H, d, J=2.4 Hz), 8.05 (1H, dd, J=7.9, 1.8 Hz), 8.32 (1H, dd, J=4.9, 1.8 Hz), 9.77 (1H, brs). Anal. C, 47.64%; H, 6.01%, N, 9.21%. Calcd for C22H26N4O3.2CH3SO3H.H2O, C, 47.67%; H, 6.00%; N, 9.27%.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with diethyl ether
  3. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-471032b9ba3241d589708d5348584d5b
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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