Ammonium Chloride → HCID 68954171, compound

HRID 1453848Notes

Reaction equation

HRID 1453848 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:11][N:12]2[CH:17]([C:18]([OH:20])=O)[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:28].[Cl-]>>[NH2:28][C:18]([CH:17]1[N:12]2[N:11]=[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:13]2[C:14](=[O:22])[N:15]([CH3:21])[CH2:16]1)=[O:20]

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 68954581HCID 68954581, compound

Product 1

HCID 68954171HCID 68954171, compound

Procedure

The title compound was prepared from 3-benzyloxy-2-ethoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-7-carboxylic acid using a procedure similar to that described in Example 2, Step 5 except that NH4Cl was used in place of 4-fluorobenzylamine, and the reaction time totaled 18 hours. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3, and the aqueous layer was extracted twice more into EtOAc. The combined organic extracts were dried over Na2SO4, concentrated in vacuo, and azeotroped with toluene to afford the title product as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 7.69 (s, 1H), 7.55 (s, 1H), 7.50-7.49 (m, 2H), 7.29-7.32 (m, 3H), 5.19 (dd, J=10.8, 24.4 Hz, 2H), 4.28-4.24 (m, 3H), 4.16 (dd, J=5.2, 13.6 Hz, 1H), 3.86-3.83 (m, 1H), 2.99 (s, 3H), 1.27 (t, J=6.8 Hz, 3H); ES MS (M+H)=373.

Workup

  1. customThe mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  2. extractionthe aqueous layer was extracted twice more into EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customazeotroped with toluene

Sources & evidence

ORD record
ord-4af26497355c4c4a8ef1be099ebb5f02
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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