Acetonitrile--water (1/1) → HCID 136237419, compound

HRID 713508Notes

Reaction equation

HRID 713508 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([CH2:8][NH:9][CH2:10][C:11]2[S:15][C:14]([C:16]#[N:17])=[CH:13][CH:12]=2)=[N:5][C:4]2[CH2:18][CH2:19][O:20][CH2:21][C:3]1=2.[F:22][C:23]1[CH:40]=[CH:39][C:26]([C:27]([CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][C:36](O)=[O:37])[CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1.CC#N.O>C(O)=O>[C:16]([C:14]1[S:15][C:11]([CH2:10][N:9]([CH2:8][C:6]2[NH:7][C:2](=[O:1])[C:3]3[CH2:21][O:20][CH2:19][CH2:18][C:4]=3[N:5]=2)[C:36](=[O:37])[CH2:35][N:32]2[CH2:33][CH2:34][CH:29]([C:27](=[O:28])[C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:40][CH:39]=3)[CH2:30][CH2:31]2)=[CH:12][CH:13]=1)#[N:17]

Participants

5

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627246HCID 136627246, compound

Product 1

HCID 136237419HCID 136237419, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Following general procedure of Example 5, the title compound was prepared (0.01 g) from 5-(((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methylamino)methyl)thiophene-2-carbonitrile and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid. 1H NMR (400 MHz, MeOD) δ ppm 8.03-8.18 (m, 2H), 7.50-7.79 (m, 1H), 7.21-7.34 (m, 2H), 7.01-7.14 (m, 1H), 4.81-4.89 (m, 2H), 4.51-4.62 (m, 2H), 4.33-4.49 (m, 4H), 3.85-4.04 (m, 2H), 3.67-3.82 (m, 2H), 3.38-3.65 (m, 1H), 3.08-3.28 (m, 2H), 2.46-2.68 (m, 2H), 1.98-2.27 (m, 4H). HRMS calculated for C28H23F1N3O4S1 550.1924. found (ESI, [M+H]+) 550.1933. MS (ESI) m/z 550.6 (M+H)+. Retention time: 3.3 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-d0eb302031844a76bdae6933ea502016
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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