HCID 11606358, compound → HCID 11713718, compound

HRID 2220675Notes

Reaction equation

[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][CH2:23][C:24]4[N:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:17][C:16]=3[C:31]3[C:32]([C:38]([OH:40])=[O:39])=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].C(C1C=C2C(C(CC3C=CC(C(=O)NCC4C=NC=CC=4)=CC=3C3C(C(O)=O)=CC(C)=CC=3)=CN2CC)=CC=1)(=N)[NH2:42].C(O)(=O)C(O)=O.NCC1N=CC=CN=1>>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][CH2:23][C:24]4[NH:29][CH2:28][CH2:27][CH2:26][N:25]=4)=[CH:17][C:16]=3[C:31]3[C:32]([C:38]([OH:40])=[O:39])=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)(=[NH:42])[NH2:2]

Participants

Reactant 3

HCID 11606358HCID 11606358, compound

HCID 17749869HCID 17749869, compound

HCID 69198542HCID 69198542, compound

Product 1

HCID 11713718HCID 11713718, compoundYield 55%

Procedure

Part A. 2′-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methyl-5′-[(pyrimidin-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid: The amide was prepared in 55% yield from the acid of Example 37, Part D following the procedure of Example 37, Part E using 2-aminomethylpyrimidine oxalate in place of 3-aminomethylpyridine. 1H NMR (500 MHz, CDCl3) δ ppm 1.38 (t, J=7.42 Hz, 3H) 2.41 (s, 3H) 3.79 (s, 2H) 4.03 (q, J=7.15 Hz, 2H) 4.86 (m, 2H) 4.96 (m, 2H) 6.67 (s, 1H) 7.03 (m, 3H) 7.17 (dd, J=15.40, 8.25 Hz, 2H) 7.24 (m, 5H) 7.41 (t, J=12 Hz, 1H) 7.56 (s, 1H) 7.60 (s, 1H) 7.74 (d, J=9.90 Hz, 1H) 7.84 (s, 1H) 8.71 (d, J=0.40 Hz, 2H). LC/MS m/z 620.4 (M+H)+.

Sources & evidence

ORD record: ord-6a53c515a2ed4862b39e530d67d49a6b
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417063B2

Reaction notes

Loading…