Hydrochloric Acid → HCID 58203940, compound

HRID 1190635Notes

Reaction equation

HRID 1190635 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[O:25][CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([C:26]5[N:27]([C:31]6[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=6[F:38])[N:28]=[CH:29][N:30]=5)[S:19][C:18]=4[C:17]=3[N:39]=2)[CH2:9]1)=O)(C)(C)C.Cl>CCOC(C)=O>[NH:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[O:25][CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([C:26]5[N:27]([C:31]6[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=6[F:38])[N:28]=[CH:29][N:30]=5)[S:19][C:18]=4[C:17]=3[N:39]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58204134HCID 58204134, compound

Product 1

HCID 58203940HCID 58203940, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulen-9-ylamino}-azetidine-1-carboxylic acid tert-butyl ester (558 mg, 1.0 mmol) was dissolved in EtOAc (10 mL). Hydrogen chloride dissolved in Ethyl acetate (EtOAc—HCl, 10 mL) was added by drop to the solution and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered to gather the solid which was washed with DCM (10 mL) to give 435 (0.43 g, yield: 87%). 1HNMR (DMSO-d6, 400 MHz): δ7.99 (s, 1H), 7.74-7.72 (m, 1H), 7.36-7.27 (m, 2H), 7.14 (s, 1H), 7.00 (d, J=8.8 Hz, 1H), 6.38-6.26 (m, 2H), 4.11-4.09 (m, 6H), 3.56 (s, 1H), 3.02 (t, J=4.8 Hz, 2H). ESI-MS: m/z=453 [M+H+]

Workup

  1. additionwas added by drop to the solution
  2. filtrationThe reaction mixture was filtered
  3. washwas washed with DCM (10 mL)

Sources & evidence

ORD record
ord-d0c565f31335465db2fbc177c79e33ba
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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