Oxalyl chloride → HCID 11511305, compound

HRID 1174984Notes

Reaction equation

HRID 1174984 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:21])=O.[CH3:24][N:25]([CH:36]1[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37]1)[C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:29]=2[N:30]=1>>[ClH:21].[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:35][C:33]3[CH:32]=[CH:31][C:29]4[N:30]=[C:26]([N:25]([CH3:24])[CH:36]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37]5)[S:27][C:28]=4[CH:34]=3)=[O:15])=[CH:16][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:35][C:33]3[CH:32]=[CH:31][C:29]4[N:30]=[C:26]([N:25]([CH3:24])[CH:36]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37]5)[S:27][C:28]=4[CH:34]=3)=[O:14])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 250196894-(Cyclohexylmethoxy)benzoic acidHCID 68772076HCID 68772076, compound

Product 2

HCID 11511305HCID 11511305, compoundYield 11%HCID 68769772HCID 68769772, compound

Procedure

The title compound is prepared by following Method C, using 4-cyclohexylmethoxy-benzoic acid (Crooks, S. L.; Merrill, B. A.; Wightman, P. D. WO 9603983 A1.) (0.46 g, 1.98 mmol), oxalyl chloride (0.66 mL, 7.62 mmol) and isomer-1 of N*2*-methyl-N*2*-(1-methyl-pyrrolidin-3-yl)-benzothiazole-2,6-diamine (0.40 g, 1.51 mmol) to afford 4-cyclohexylmethoxy-N-{2-[methyl-(1-methyl-pyrrolidin-3-yl)-amino]-benzothiazol-6-yl}-benzamide (0.083 11%). The material is dissolved in EtOH and treated with 1.0 M HCl in EtOH (0.17 mL). Heptane is added and the resulting solid is collected to give 0.052 g (59%) of the hydrochloride salt. LC/MS: Retention time=5.38 min; (m/z): calcd for C27H34N4O2S (M+H)+: 479.7; found: 479.3.

Sources & evidence

ORD record
ord-6e5ef8b35b33474c8cf2877dd1af5314
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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