Hydrochloric Acid → HCID 73054597, compound

HRID 2205670Notes

Reaction equation

HRID 2205670 reaction equation
C[O:2][C:3]1[C:12]([C:13]2[O:17][C:16]([C@@H:18]([NH:28][C:29]([CH:31]3[CH2:34][N:33]([CH3:35])[CH2:32]3)=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:27])[CH2:25][CH3:26])=[N:15][CH:14]=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:35][N:33]1[CH2:34][CH:31]([C:29]([NH:28][C@H:18]([C:16]2[O:17][C:13]([C:12]3[C:3](=[O:2])[NH:4][C:5]4[C:10]([CH:11]=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:14][N:15]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:27])[CH2:25][CH3:26])=[O:30])[CH2:32]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 72793856HCID 72793856, compound

Product 1

HCID 73054597HCID 73054597, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-N-(1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-oxononyl)-1-methylazetidine-3-carboxamide (0.05 mmol, 1 eq), prepared as described above, in DCM (1 mL) was treated with 0.2 mL of HCl 4N in dioxane. The mixture was stirred 1 h at room temperatures, then concentrated and purified by RP-HPLC using water (+0.01% TFA) and MeCN (+0.01% TFA) as eluents (column C18). The pooled product fractions were lyophilized and the product was obtained as a white solid. MS (ES) C26H32N4O4 requires: 464.58, found: 465. 1H-NMR (400 MHz, DMSO-d6) δ: 12.21 (1 H, s), 9.83 (1 H, bs), 8.89-8.82 (1 H, m), 8.26 (1 H, s), 7.83 (1 H, d, J=7.6 Hz), 7.78 (1 H, s), 7.55 (1 H, t, J=7.2 Hz), 7.38 (1 H, d, J=8.4 Hz), 7.25 (1 H, t, J=7.6 Hz), 5.09 (1 H, bs), 4.36 (1 H, bs), 4.22-4.20 (1 H, m), 4.11 (1 H, bs), 3.98-3.92 (1 H, m), 3.57-3.55 (1 H, m, partially overlaps with water), 2.82 (3 H, s), 2.42-2.37 (4 H, m), 1.96-1.92 (1 H, m), 1.83-1.80 (1 H, m), 1.48-1.44 (2 H, m), 1.35-1.33 (4 H, m), 0.89 (3 H, t, J=7.2 Hz).

Workup

  1. concentrationconcentrated
  2. custompurified by RP-HPLC
  3. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-bfdb049bc8f14e21a2b9365324cc63d0
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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