1,2-Dichloroethane → HCID 59589900, compound

HRID 1971587Notes

Reaction equation

HRID 1971587 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:33]=[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([C:24]5[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=5)[C:27](O)=[O:28])[N:18]4[N:17]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1.C(Cl)CCl.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1>>[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([C:23]3[N:18]4[N:17]=[C:16]([NH:15][C:12]5[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]6[CH2:2][CH2:3][CH2:4][CH2:5]6)=[CH:10][CH:11]=5)[N:33]=[C:19]4[CH:20]=[CH:21][CH:22]=3)[CH:25]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59589749HCID 59589749, compound

Product 1

HCID 59589900HCID 59589900, compound

Procedure

To a stirred solution of 3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzoic acid (50 mg, 0.113 mmol), 4-chlorobenzylamine (27.5 μL, 0.226 mmol), EDC (44 mg, 0.226 mmol) and di-isopropylethylamine (98.5 μL, 0.564 mmol) was added HOBt (31 mg, 0.226 mmol). The mixture was stirred overnight at room temperature, and the desired product purified by preparatory HPLC. RT: 4.63 min, MI: 567.31, Method: basic. 1H NMR (DMSO, 300 MHz): 9.43 (s, 1H), 9.22 (t, 1H), 8.58 (s, 1H), 8.19 (t, 1H), 8.03 (d, 1H), 7.63 (m, 6H), 7.36 (s, 3H), 7.24 (dd, 1H), 6.84 (d, 2H), 4.50 (d, 2H), 3.99 (t, 2H), 2.81 (t, 2H), 2.50 (d, 2H), 2.36 (s, 2H), 1.69 (m, 4H).

Workup

  1. customthe desired product purified by preparatory HPLC

Sources & evidence

ORD record
ord-ac344891547e467895cbbd4070aa8fa8
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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