Hydrochloric Acid → HCID 136355281, compound

HRID 2062304Notes

Reaction equation

HRID 2062304 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:25]([C@H:27]3[CH2:31][CH2:30][CH2:29][O:28]3)=[O:26])[CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1.[ClH:33]>CCOCC>[ClH:33].[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:19][CH2:20][CH:21]([NH:24][C:25]([C@H:27]3[CH2:31][CH2:30][CH2:29][O:28]3)=[O:26])[CH2:22][CH2:23]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136121371HCID 136121371, compound

Product 1

HCID 136355281HCID 136355281, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(R)-Tetrahydro-furan-2-carboxylic acid {1-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperidin-4-yl}-amide (303 mg, 0.701 mmol) was dissolved in 9 mL 2:1 dry ether/dry CH2Cl2 and 2.0 M HCl in ether added dropwise (0.35 mL, 0.70 mmol), producing a white precipitate which was collected by filtration to give (R)-Tetrahydro-furan-2-carboxylic acid {1-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperidin-4-yl}-amide hydrochloride (268 mg, 82%). LC/MS: m/z 433.5 (M+H)+ at 2.26 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.20 (dd, J=7.8, 1.2 Hz, 1H), 8.00 (d, J=8.6 Hz, 1H), 7.80-7.79 (m, 2H), 7.51-7.47 (m, 2H), 7.15 (d, J=8.2 Hz, 1H), 7.05-7.01 (m, 1H), 4.66-4.63 (m, 2H), 4.21 (dd, J=8.2, 5.2 Hz, 1H), 4.12-4.03 (m, 1H), 3.91-3.84 (m, 1H), 3.78-3.70 (m, 1H), 3.59 (t, J=12.3 Hz, 2H), 2.54 (s, 3H), 2.16-2.05 (m, 1H), 1.97-1.94 (m, 2H), 1.89-1.72 (m, 5H).

Workup

  1. additionadded dropwise (0.35 mL, 0.70 mmol)
  2. customproducing a white precipitate which
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-67b7280947d841d0af89d865b733f312
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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