Hydrochloric Acid → HCID 118483173, compound

HRID 1773348Notes

Reaction equation

HRID 1773348 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:16]([CH2:39][C:40]([OH:42])=[O:41])[C:17](=[O:38])[C:18]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[C:23]([F:29])[CH:22]=3)[N:20]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.Cl>CC(=O)OCC>[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:16]([CH2:39][C:40]([OH:42])=[O:41])[C:17](=[O:38])[C:18]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[C:23]([F:29])[CH:22]=3)[N:20]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118483152HCID 118483152, compound

Product 1

HCID 118483173HCID 118483173, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of [2-(4-tert-butoxycarbonylamino-piperidin-1-yl)-4-(4-cyano-3-fluoro-phenyl)-5-(4-methoxy-phenyl)-6-oxo-6H-pyrimidin-1-yl]-acetic acid (100 mg, 0.15 mmol) in EA (10 mL) was added a 5N HCl solution in EA (5 mL). The reaction mixture was stirred at RT for 2 h, and the solvent was concentrated in vacuo. The residue was purified by preparative HPLC to give 25 mg of the title product as HCl salt (32%). 1H NMR (400 MHz, CD3OD): δ 1.53-1.56 (m, 2H), 2.00-2.03 (m, 2H), 3.00-3.07 (m, 2H), 3.35-3.39 (m, 1H), 3.67 (s, 3H), 4.70 (s, 2H), 4.76-4.77 (m, 2H), 6.74 (d, J=8.4 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 7.17 (d, J=8.4 Hz, 1H), 7.26 (d, J=10.0 Hz, 1H), 7.50 (dd, J=7.2, 8.0 Hz, 1H). [M+H] Calc'd for C25H24FN5O4, 478. Found, 478.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d36171a974f143849d10371bc6a069a7
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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