Oxalyl chloride → HCID 76601344, compound

HRID 1174904Notes

Reaction equation

HRID 1174904 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.[CH3:19][N:20]([CH3:36])[CH:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]3[CH:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:29]=3[N:30]=2)[CH2:22]1>>[CH3:19][N:20]([CH3:36])[CH:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]3[CH:34]=[C:33]([NH:35][C:10]([C:2]4[S:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[CH:3]=4)=[O:12])[CH:32]=[CH:31][C:29]=3[N:30]=2)[CH2:22]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 76601344HCID 76601344, compoundYield 31.1%

Procedure

Prepare according to Method C (Example 9), using benzothiophene-2-carboxylic acid (123 mg, 0.685 mmol), oxalyl chloride (300 μL, 3.44 mmol), and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (100 mg, 0.381 mmol) to afford the title compound (50 mg, 31%). mass spectrum (m/e): 423.0 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 10.53 (s, 1H), 8.35 (s, 1H), 8.25 (d, 1H, J=2.2 Hz), 8.06 (dd, 1H, J=6.5, 1.9 Hz), 8.01 (dd, 1H, J=6.2, 2.7 Hz), 7.55 (dd, 1H, J=8.8, 2.2 Hz), 7.50-7.43 (m, 3H), 3.72 (m, 1H), 3.63 (m, 1H), 3.48 (m, 1H), 3.31 (m, 1H), 2.90 (m, 1H), 2.22-2.17 (m, 7H), 1.92 (m, 1H).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-d5372e07c947475881c75faa4d59cbb5
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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