Oxalyl chloride → 5-Chloro-benzofuran-2-carboxylic acid [2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-amide

HRID 1174896Notes

Reaction equation

HRID 1174896 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=2[CH:13]=1.C(Cl)(=O)C(Cl)=O.[CH3:20][N:21]([CH3:37])[CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]3[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:30]=3[N:31]=2)[CH2:23]1>>[CH3:20][N:21]([CH3:37])[CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]3[CH:35]=[C:34]([NH:36][C:10]([C:8]4[O:9][C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=5[CH:7]=4)=[O:12])[CH:33]=[CH:32][C:30]=3[N:31]=2)[CH2:23]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 9378385-Chloro-1-benzofuran-2-carboxylic acidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 766013385-Chloro-benzofuran-2-carboxylic acid [2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-amideYield 43.5%

Procedure

Prepare according to Method C (Example 9), using 5-chlorobenzofuran-2-carboxylic acid (109 mg, 0.554 mmol), oxalyl chloride (300 μL, 3.43 mmol), and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (100 mg, 0.381 mmol) to afford the title compound (73 mg, 43%). mass spectrum (m/e): 441.0 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 8.26 (d, 1H, J=1.8 Hz), 7.93 (d, 1H, J=2.2 Hz), 7.76 (d, 1H, J=8.6 Hz), 7.73 (d, 1H, J=0.9 Hz), 7.60 (dd, 1H, J=8.8, 2.2 Hz), 7.52 (dd, 1H, J=8.8, 2.2 Hz), 7.45 (d, 1H, J=8.4 Hz), 3.72 (dd, 1H, J=9.5, 7.3 Hz), 3.63 (m, 1H), 3.48 (m, 1H), 3.27 (m, 1H), 2.89 (m, 1H), 2.22-2.15 (m, 7H), 1.91 (m, 1H).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-4b09e17fb9a4467dbb64dfe35da68717
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

Loading…