Hydrochloric Acid → HCID 68869206, compound

HRID 1783379Notes

Reaction equation

HRID 1783379 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:25]1[C:34]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1)[CH:22]1[CH2:24][CH2:23]1)[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(C)(C)C.[ClH:43].CCOCC>O1CCOCC1>[ClH:43].[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:25]1[C:34]([CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[N:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1)[CH:22]1[CH2:24][CH2:23]1)[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57590386HCID 57590386, compound

Product 1

HCID 68869206HCID 68869206, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (±)-{3-[[(3-benzylquinoxalin-2-yl)cyclopropylmethyl]-(4-methyl-benzoyl)-amino]-propyl}carbamic acid tert-butyl ester 7 (0.40 g, 0.71 mmol) in dioxane (5 mL) at rt was added 4 N HCl in dioxane (2.0 mL, 8 mmol). The reaction mixture was stirred overnight. It was added with Et2O and the precipitated solid was collected, washed with Et2O and dried in vacuo over P2O5 to give 8 (0.32 g, 90%). 1H NMR (CD3OD) δ 8.15 (m, 2H), 7.87 (m, 2), 7.36 (m, 4H), 7.22 (m, 5H), 6.56 (m, 1H), 5.52 (m, 1H), 4.75 (m, 1H), 4.23 (m, 1H), 3.69 (m, 2H), 3.65 (s, 3H), 3.06 (m, 1H), 2.39 (m, 4H), 2.10 (m, 1H), 1.98 (m, 1H), 1.85 (m, 1H), 1.46 (m, 1H), 0.63 (m, 2H), 0.46 (m, 1H), 0.29 (m, 2H); 13C NMR (CD3OD) δ 155.5, 142.3, 141.2, 135.2, 131.9,130.5, 130.1, 130.0, 129.8, 129.6, 128.0, 127.3, 68.5, 43.2, 41.8, 38.9, 30.5, 21.7, 14.4, 5.78; MS (ESI), (M+H)+465.31.

Workup

  1. customthe precipitated solid was collected
  2. washwashed with Et2O
  3. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-1cb813fa1afc453b986fe24bc8525349
Source dataset
uspto-grants-2009_03
Patent number
US07501416B2

Reaction notes

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