Oxalyl chloride → N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-3-naphthalen-2-yl-acrylamide

HRID 1174899Notes

Reaction equation

HRID 1174899 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([OH:15])=O.C(Cl)(=O)C(Cl)=O.[CH3:22][N:23]([CH3:39])[CH:24]1[CH2:28][CH2:27][N:26]([C:29]2[S:30][C:31]3[CH:37]=[C:36]([NH2:38])[CH:35]=[CH:34][C:32]=3[N:33]=2)[CH2:25]1>>[CH3:22][N:23]([CH3:39])[CH:24]1[CH2:28][CH2:27][N:26]([C:29]2[S:30][C:31]3[CH:37]=[C:36]([NH:38][C:13](=[O:15])[CH:12]=[CH:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH:35]=[CH:34][C:32]=3[N:33]=2)[CH2:25]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 6077373-(Naphthalen-2-yl)acrylic acidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 68774570N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-3-naphthalen-2-yl-acrylamideYield 96%

Procedure

Prepare according to Method C (Example 9), using 3-(2-naphthyl)acrylic acid (69 mg, 0.348 mmol), oxalyl chloride (150 μL, 1.72 mmol), and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (60 mg, 0.229 mmol) to afford the title compound (97 mg, 96%). mass spectrum (m/e): 442.0 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 10.27 (s, 1H), 8.30 (d, 1H, J=1.3 Hz), 8.14 (s, 1H), 8.00-7.92 (m, 3H), 7.78 (dd, 1H, J=8.5, 1.6 Hz), 7.71 (d, 1H, J=15.6), 7.59-7.54 (m, 2H), 7.45-7.42 (m, 2H), 6.97 (d, 1H, J=15.4 Hz), 3.71 (t, 1H, J=8.1 Hz), 3.62 (t, 1H, J=7.9 Hz), 3.47 (m, 1H), 3.26 (m, 1H), 2.89 (m, 1H), 2.21-2.17 (m, 7H), 1.94-1.86 (m, 1H).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-9d23cc35240c4df8b890a5a6e56a5944
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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