Hydrochloric Acid → HCID 69001658, compound

HRID 1909744Notes

Reaction equation

HRID 1909744 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:29].CCOCC>O1CCOCC1>[ClH:29].[I:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:16][CH:17]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68996388HCID 68996388, compound

Product 1

HCID 69001658HCID 69001658, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5. To a 20 mL vial which contained a solution of the product from step 4 (200 mg, 0.4 mmol) in dioxane was added HCl (4 N in dioxane, 2 mL) at 0° C. The mixture was allowed to warm to rt and stir at rt for 16 h. The solvent was reduced to 1 mL and ether (15 mL) was added to this vial. The resulting solid was filtered out and dried under vacuo to yield the title product (150 mg, 95%); LCMS; APCI+ 99%, Calcd: 393.3; Found m/z: 392.3 (M−1); 1H NMR (400 MHz, DMSO-d6); δ 1.68-1.77 (m, 1H), 1.86-2.04 (m, 2H), 2.05-2.16 (m, 1H), 3.14-3.23 (m, 2H), 3.84 (s, 2H), 3.83-3.89 (m, 1H), 4.07-4.11 (m, 1H), 4.20 (dd, J1=10.4 Hz, J2=3.6 Hz, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.01 (d, J=8.0 Hz, 2H), 7.15 (d, J=8.8 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H):

Workup

  1. additionwas added to this vial
  2. filtrationThe resulting solid was filtered out
  3. customdried under vacuo

Sources & evidence

ORD record
ord-20dd425f35cc409c8f2b0943a3cfb182
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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