Hydrochloric Acid → HCID 131731923, compound

HRID 529343Notes

Reaction equation

HRID 529343 reaction equation
C(OC([N:8]([CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]=2[C:35]#[N:36])[CH2:21][CH2:20]1)[C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:37].C(OCC)C>C(Cl)Cl>[ClH:37].[ClH:37].[C:35]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:26]=1[CH2:25][N:22]1[CH2:23][CH2:24][CH:19]([CH2:18][NH:8][C@@H:9]2[CH2:11][C@H:10]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:20][CH2:21]1)[C:30]([OH:32])=[O:31])#[N:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 683884464-((4-(((Tert-butoxycarbonyl)((trans)-2-phenylcyclopropyl)amino) methyl)piperidin-1-yl)methyl)-3-cyanobenzoic acid

Product 1

HCID 131731923HCID 131731923, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-((4-(((tert-butoxycarbonyl)((trans)-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)methyl)-3-cyanobenzoic acid (400 mg, 0.817 mmol) in DCM (5 mL) was added HCl in diethyl ether (5 mL, 0.817 mmol) at 0° C. and stirred at RT for 2 h. The reaction mixture was concentrated and the residue was triturated with diethyl ether (2×10 mL) and dried to afford 3-cyano-4-((4-((((trans)-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)methyl)benzoic acid, dihydrochloride (250 mg, 0.538 mmol, 65.9% yield) as white solid. LCMS (ES) m/z: 390.09 (M+H)+. 1HNMR (400 MHz in D2O): δ 8.489 (bs, 1H) 8.342 (d, J=8 Hz, 1H), 7.866 (d, J=8 Hz, 1H), 7.400-7.291 (m, 3H), 7.209 (d, J=8 Hz, 2H), 4.624 (s, 2H), 3.683 (d, J=10.8 Hz, 2H), 3.269-3.214 (m, 4H), 2.979-2.997 (m, 1H), 2.526-2.577 (m, 1H), 2.107 (d, J=14.8, 3H), 1.528-1.618 (m, 3H), 1.434 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was triturated with diethyl ether (2×10 mL)
  3. customdried

Sources & evidence

ORD record
ord-b6c3a9e8e72645bbb0290d024ffb265e
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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