Acetonitrile--water (1/1) → HCID 136237472, compound

HRID 713518Notes

Reaction equation

HRID 713518 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][CH:20]([F:35])[CH2:21][NH:22][CH2:23][C:24]1[NH:25][C:26](=[O:34])[C:27]2[CH2:33][O:32][CH2:31][CH2:30][C:28]=2[N:29]=1.CC#N.O>C(O)=O>[C:1]([CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]([N:22]([CH2:21][CH:20]([F:35])[F:19])[CH2:23][C:24]2[NH:25][C:26](=[O:34])[C:27]3[CH2:33][O:32][CH2:31][CH2:30][C:28]=3[N:29]=2)=[O:18])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 71227212HCID 71227212, compoundHCID 136627267HCID 136627267, compound

Product 1

HCID 136237472HCID 136237472, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The title compound (0.07 g) was prepared following the general procedure of Example 1 from 2-(4-benzoylpiperidin-1-yl)acetic acid and 2-((2,2-difluoroethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one. 1H NMR (400 MHz, MeOD) δ ppm 7.89-8.03 (m, 2H), 7.44-7.66 (m, 3H), 5.88-6.43 (m, 1H), 4.61-4.69 (m, 1H), 4.53-4.60 (m, 1H), 4.40-4.48 (m, 1H), 3.78-4.23 (m, 5H), 3.36-3.59 (m, 2H), 3.02-3.18 (m, 1H), 2.83-2.93 (m, 1H), 2.54-2.69 (m, 3H), 2.13-2.36 (m, 2H), 1.65-1.97 (m, 3H), 1.37-1.54 (m, 1H). HRMS calculated for C24H29F2N4O4 475.2157. found (ESI, [M+H]+) 475.2180. MS (ESI) m/z 475.2. (M+H)+. Retention time: 3.04 min (5-95% CH3CN/H2O over 7.75 min with 0.1% formic acid, Inertsil ODS3 100×3 mm C18 column with flow rate of 1.0 mL/min).

Sources & evidence

ORD record
ord-4fdb1fc1ff0f446bb890f59d803428df
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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