Hydrochloric Acid → HCID 69939587, compound

HRID 1265224Notes

Reaction equation

HRID 1265224 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[NH:8][C@H:9]([C:35]([O:37][CH3:38])=[O:36])[CH2:10][O:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]([NH:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[O:26])[CH:19]=3)[CH:15]=[CH:16][CH:17]=2)C=CC=CC=1.[ClH:51]>O1CCOCC1>[ClH:51].[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:27][C:25]([NH:24][C:20]1[CH:19]=[C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C@@H:9]([C:35]([O:37][CH3:38])=[O:36])[NH2:8])[CH:13]=2)[CH:23]=[CH:22][CH:21]=1)=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59050115HCID 59050115, compound

Product 1

HCID 69939587HCID 69939587, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The compound of Example 9 (1369,8 mg, 2.07 mmol, 1 equiv) was dissolved in dioxane (4 mL) and treated with a 1M solution of hydrochloric acid in dioxane (4.5 mL, 4.5 mmol, 2.2 equiv) at room temperature. The reaction mixture was stirred for 3.5 h at ambient temperature. The solvents were removed under reduced pressure and the crude product was titurated with diethylether. The white precipitate was filtered off and dried in vacuuo. Yield 615.4 mg, 65.2% of a white solid. 1H NMR (DMSO, 200 MHz) δ 9.69 (s, 1H-NH); 8.95 (s, 2H); 8.79 (d, 1H); 8.52-8.38 (m, 1H); 7.99-7.72 (m, 3H); 7.55-7.32 (m, 4H); 7.25-7.17 (m, 3H); 7.02 (d, 1H); 4.82-4.59 (m, 2H); 4.51-4.40 (m, 1H); 3.80 (s, 3H), 2.55 (s, 2H). MS (ESI) 443 (M+Na), 421 (M+H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. filtrationThe white precipitate was filtered off
  3. customdried in vacuuo

Sources & evidence

ORD record
ord-f05af4375f134a14b75891935c130940
Source dataset
uspto-grants-2003_04
Patent number
US06545029B2

Reaction notes

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