4-Methylmorpholine → HCID 178441678, compound

HRID 2067144Notes

Reaction equation

HRID 2067144 reaction equation
[K].[CH3:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]3[N:28]=[N:27][NH:26][N:25]=3)=[CH:16][CH:17]=2)[C:9]([CH2:29][OH:30])=[C:8]([Cl:31])[N:7]=1.[CH3:32][O:33][C@@H:34]1[C@@H:38]([O:39][N+:40]([O-:42])=[O:41])[CH2:37][C@H:36]([C:43](O)=[O:44])[CH2:35]1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:32][O:33][C@@H:34]1[C@@H:38]([O:39][N+:40]([O-:42])=[O:41])[CH2:37][C@H:36]([C:43]([O:30][CH2:29][C:9]2[N:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:24]4[NH:28][N:27]=[N:26][N:25]=4)=[CH:16][CH:17]=3)[C:6]([CH2:5][CH2:4][CH2:3][CH3:2])=[N:7][C:8]=2[Cl:31])=[O:44])[CH2:35]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98471641H-Imidazole-5-methanol, 2-butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-, potassium salt (1:1)HCID 58443614(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid2×

Product 1

HCID 178441678HCID 178441678, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of potassium losartan (974 mg, 2.11 mmol), (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid (intermediate 1, 429 mg, 2.09 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (447 mg, 2.33 mmol), and N-methylmorpholine (0.50 mL, 4.6 mmol) was dissolved in dichloromethane (20 mL) and stirred for 2 days with catalytic amounts of 4-(dimethylamino)pyridine. 1H NMR (500 MHz, CDCl3) δ 0.84 (t, J=7.3 Hz, 3H), 1.28 (sextet, J=7.3 Hz, 2H), 1.56 (quintet, J=7.3 Hz, 2H), 1.78-1.84 (m, 1H), 1.88-1.92 (m, 1H), 2.08-2.15 (m, 1H), 2.30-2.36 (m, 1H), 2.38 (t, J=6.7 Hz, 2H), 2.71 (quintet, J=8.2 Hz, 1H), 3.26 (s, 3H), 3.70-3.75 (m, 1H), 4.87 (d, J=13.9 Hz, 1H), 4.91 (d, J=13.7 Hz, 1H), 5.13 (s, 2H), 5.15-5.19 (m, 1H), 6.77 (d, J=8.0 Hz, 2H), 7.10 (d, J=8.2 Hz, 2H), 7.41 (d, J=7.8 Hz, 1H), 7.52 (td, J=1.4, 7.6 Hz, 1H), 7.61 (td, J=1.4, 7.6 Hz, 1H), 7.84 (dd, J=0.9, 7.7 Hz, 1H); LC-MS: m/z 610.4 (M+H).

Sources & evidence

ORD record
ord-a697b4ccc7a44b809b0174557fceaf32
Source dataset
uspto-grants-2012_10
Patent number
US08293777B2

Reaction notes

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