2-Morpholinoethylamine → N1-(2-Morpholinoethyl)-N3-(4-(piperidin-1-yl)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl) pyridin-2-yl)phenyl)isophthalamide

HRID 625237Notes

Reaction equation

HRID 625237 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][CH:42]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[NH:28][C:29]([C:31]2[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=2)[C:34](O)=[O:35])=[O:30])[CH:11]=1)=[O:9].FC(F)(F)C1C=C(C=CC=1)CNC(C1C=CN=C(C2C=C(N3CCCCC3)C=CC=2NC(=O)C2C=CC=C(C(N(CCC(NCCOC)=O)C)=O)C=2)C=1)=O.[O:99]1[CH2:104][CH2:103][N:102]([CH2:105][CH2:106][NH2:107])[CH2:101][CH2:100]1>>[O:99]1[CH2:104][CH2:103][N:102]([CH2:105][CH2:106][NH:107][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][CH:39]=[C:31]([C:29]([NH:28][C:17]3[CH:18]=[CH:19][C:20]([N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:21][C:16]=3[C:12]3[CH:11]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]4[CH:40]=[CH:41][CH:42]=[C:3]([C:2]([F:43])([F:1])[F:44])[CH:4]=4)[CH:15]=[CH:14][N:13]=3)=[O:30])[CH:32]=2)[CH2:101][CH2:100]1

Participants

4

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 665867843-((2-(4-((3-(Trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzoic acidHCID 66588102N1-(2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)-N3-(3-(2-methoxyethylamino)-3-oxopropyl)-N3-methylisophthalamide

Product 1

HCID 69630859N1-(2-Morpholinoethyl)-N3-(4-(piperidin-1-yl)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl) pyridin-2-yl)phenyl)isophthalamide

Procedure

This compound was prepared from 3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)-benzoic acid 4.1e using the procedure described for the preparation of N1-(2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)-N3-(3-(2-methoxyethylamino)-3-oxopropyl)-N3-methylisophthalamide 4.2. 2-Morpholinoethanamine was used as the amine component in this coupling. 1H-NMR (300 MHz, DMSO-d6, ppm) δ 12.60 (s, 1H), 9.68 (s, 1H), 9.57 (t, 1H), 9.00 (d, J=5.1 Hz, 1H), 8.95 (t, 1H), 8.50 (s, 1H), 8.36 (s, 2H), 8.09 (t, 2H), 7.85 (d, J=5.1 Hz, 1H), 7.64 (m, 6H), 7.28 (s, 1H), 4.63 (d, J=6.0 Hz, 2H), 4.02 (m, 4H), 3.69 (m, 6H), 3.43 (m, 8H), 1.65 (m, 6H). MS (ES, m/z): 715 [M+H]+.

Sources & evidence

ORD record
ord-7789a44954bb45c18fd0cfd36f28ef45
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

Loading…