Hydrochloric Acid → HCID 22184652, compound

HRID 2414537Notes

Reaction equation

HRID 2414537 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:25]=[C:24]([O:26]COCC[Si](C)(C)C)[C:23]4[C:18](=[C:19]([N:37]5[CH2:43][CH2:42][CH2:41][N:40]([CH3:44])[CH2:39][CH2:38]5)[CH:20]=[C:21]([O:35][CH3:36])[CH:22]=4)[N:17]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[OH-].[Na+]>CO>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]([C:16]3[NH:17][C:18]4[C:23]([C:24](=[O:26])[CH:25]=3)=[CH:22][C:21]([O:35][CH3:36])=[CH:20][C:19]=4[N:37]3[CH2:43][CH2:42][CH2:41][N:40]([CH3:44])[CH2:39][CH2:38]3)=[O:15])=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23533311HCID 23533311, compound

Product 1

HCID 22184652HCID 22184652, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-methoxy-8-(4-methyl-[1,4-]diazepan-1-yl)-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide (Reference Example 27d) (0.989 g, 1.59 mmol) in 20 mL methanol was poured into 300 mL 0.05 N hydrochloric acid. The clear dark yellow solution became cloudy within 5 minutes. The mixture was stirred at room temperature for 45 minutes and then adjusted to pH 7 with 10% sodium hydroxide. The resulting yellow precipitate was isolated by filtration, washed with water, and dried under high vacuum to afford the desired product as a yellow solid (0.629 g, 80%). 1H NMR (300 MHz, DMSO, d6) δ 9.97 (s, 1H,C(O)NH), 7.67 (d, 2H, Jo=8.8 Hz, ArH2′ & H6′), 7.47 (bs, 1H, ArH5), 7.00 (s, 1H, C═CH), 6.99 (d, 2H, Jo=8.8 Hz, ArH3′ & H5′), 6.71 (bs, 1H, ArH7), 3.85 (s, 3H, OCH3), 3.75 (t, 4H, J=4.6 Hz, OCH2CH2N), 3.70 (bs, 2H, ArNCH2CH2CH2NCH3), 3.55 (bs, 2H, ArNCH2CH2NCH3), 3.09 (t, 4H, J=4.6Hz, OCH2CH2N), 2.95 (bs, 2H, ArNCH2CH2NCH3), 2.73 (bs, 2H, ArNCH2CH2CH2NCH3), 2.36 (s, 3H, NCH3), 2.07 (bs, 2H, ArNCH2CH2CH2NCH3); Mass Spec.: calc. for [C27H33N5O4+H]+ Theor. m/z=492; Obs.=492. Analysis for C27H33N5O4.1.0eqHCl.0.3eqH2O: Calculated C, 60.79; H, 6.54; N, 13.13. Found C, 60.82; H, 6.53; N, 13.17.

Workup

  1. customwithin 5 minutes
  2. customThe resulting yellow precipitate was isolated by filtration
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-b72a2df63b474e16be2abe763c5ea23b
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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