Hydrochloric Acid → HCID 178448923, compound

HRID 1030063Notes

Reaction equation

HRID 1030063 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:5]([C:50]([O:52]CC)=[O:51])=[CH:4][N:3]=1.O.[OH-].[Li+].[ClH:58]>CO.C1COCC1.O>[ClH:58].[CH3:1][C:2]1[N:7]=[C:6]([N:8]([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[C:5]([C:50]([OH:52])=[O:51])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 19791910Ethyl 2-methyl-4-{N-butyl-N-[{2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl}methyl]amino}pyrimidine-5-carboxylate

Product 1

HCID 178448923HCID 178448923, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 1B (0.6 g, 0.842 mmole) was dissolved in 4 ml of methanol and 6 ml of THF. A solution of 180 mg of lithium hydroxide monohydrate in 1.5 ml of water was added and the mixture was refluxed for 5 hours. After cooling, 1 ml of concentrated hydrochloric acid was added and the mixture was stirred at room temperature for 2 hours. The resulting solution was concentrated under vacuum and 2 ml of water and 3 ml of ether was added to the residue. An oil which was insoluble in both layers formed. The oil was separated and crystallized from acetonitrile to provide 0.289 g of the desired product. M.p. 155°-158° C. 1H NMR (CD3OD) δ0.95 (t, 3H, J=7 Hz), 1.30 (m, 2H), 1.69 (m, 2H), 2.60 (s, 3H), 3.70 (m, 2H), 5.08 (m, 2H), 7.10 (d, 2H), 7.20 (s, 2H), 7.55 (d, 2H), 7.5-7.7 (m, 4H), 8.55 (s, 1H).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureAfter cooling
  3. concentrationThe resulting solution was concentrated under vacuum and 2 ml of water and 3 ml of ether
  4. additionwas added to the residue
  5. customformed
  6. customThe oil was separated
  7. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-d5a8bbf4cb3941c09e620e8426241ba5
Source dataset
uspto-grants-1992_04
Patent number
US05104877

Reaction notes

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