Hydrochloric Acid → HCID 178479237, compound

HRID 1033377Notes

Reaction equation

HRID 1033377 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][CH:13]1[CH2:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[NH:41][N:40]=[N:39][N:38]=3)=[CH:27][CH:26]=2)[C:14]1=[O:42])=[O:11])=O)(C)(C)C.[ClH:43]>CO>[ClH:43].[NH2:8][CH2:9][C:10]([NH:12][CH:13]1[CH2:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[NH:41][N:40]=[N:39][N:38]=3)=[CH:27][CH:26]=2)[C:14]1=[O:42])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178453800HCID 178453800, compound

Product 1

HCID 178479237HCID 178479237, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The intermediate obtained in Step C (109 mg, 0.196 mmol) was dissolved in 2 mL of methanol and treated with 0.1 mL of concentrated hydrochloric acid. The reaction mixture was stirred at room temperature for 16 hours then solvents were removed under vacuum and the residue redissolved in water and washed with ethyl acetate. The aqueous layer was separated and the solvent removed under vacuum to yield 87 mg (0.17 mmol, 88%) of the title compound. 1H NMR (200 MHz, CD3OD): 2.10 (m, 1 H), 2.48 (m, 3 H), 3.68 (s,2 H), 4.37 (m,1 H), 4.84 (d,14 Hz,1 H), 5.22 (d,14 Hz,1 H), 6.9-7.7 (m,12 H). FAB-MS: calculated for C26H25N7O2 467; found 468 (M+H,100%).

Workup

  1. customsolvents were removed under vacuum
  2. dissolutionthe residue redissolved in water
  3. washwashed with ethyl acetate
  4. customThe aqueous layer was separated
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-7d9e19a277d240bdab5eea343e306f01
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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