Morpholine → HCID 178424460, compound

HRID 536951Notes

Reaction equation

HRID 536951 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([CH:20]=O)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCOC(C)=O.C(Cl)Cl>CO.C(Cl)Cl>[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([CH2:20][N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 21226138Dichloromethane ethylacetateHCID 178424467HCID 178424467, compound

Product 1

HCID 178424460HCID 178424460, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 21, step (b) using 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(4-formyl-tetrahydro-pyran-4-yl)-phenyl]-amide (as prepared in the previous step, 40.0 mg, 0.0921 mmol), morpholine (13 μL, 0.14 mmol) and sodium triacetoxyborohydride (5.2 mg, 0.14 mmol). Silica gel chromatography (10-20% EtOAc/DCM then 1-2% MeOH/DCM) afforded the title compound (20 mg, 43%) as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 12.61 (s, 1H), 9.70 (s, 1H), 8.33 (d, 1H, J=8.6 Hz), 7.75 (s, 1H), 7.28 (dd, 1H, J=8.6, 2.3 Hz), 7.16 (d, 1H, J=2.3 Hz), 5.78 (m, 1H), 3.79 (m, 2H), 3.59 (m, 2H), 3.50-3.62 (m, 4H), 2.45 (s, 2H), 2.25-2.31 (m, 2H), 2.11-2.22 (m, 8H), 1.93 (m, 2H), 1.61 (t, 2H, J=6.3 Hz), 1.13 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C29H37N5O3, 504.3 (M+H). found 504.3.

Workup

  1. customThe title compound was prepared by the procedure of Example 21, step (b)

Sources & evidence

ORD record
ord-ab5d2658d8454f40bfa05930b77284b4
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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