Ethylamine → HCID 59592851, compound

HRID 2262209Notes

Reaction equation

HRID 2262209 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14](O)=[O:15])=[CH:8][C:6]=2[N:7]=1.[CH2:26]([NH2:28])[CH3:27].CC1(C)C(C)(C)OB([C:37]2[CH:45]=[CH:44][CH:43]=[C:42]3[C:38]=2[CH:39]=[N:40][NH:41]3)O1>>[NH:41]1[C:42]2[C:38](=[C:37]([C:2]3[N:3]=[C:4]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[C:5]4[S:10][C:9]([C:11]5[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=5)[C:14]([NH:28][CH2:26][CH3:27])=[O:15])=[CH:8][C:6]=4[N:7]=3)[CH:45]=[CH:44][CH:43]=2)[CH:39]=[N:40]1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 86618428HCID 86618428, compound

Product 1

HCID 59592851HCID 59592851, compound

Procedure

3-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzoic acid (55 mg) was reacted with ethylamine via General Procedure B to yield 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-ethylbenamide. Crude 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-ethylbenamide (59 mg) was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A to yield 14.5 mg of 329. MS (Q1) 485.1 (M)+

Workup

  1. customto yield 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-ethylbenamide

Sources & evidence

ORD record
ord-5342c7c30f6242d49f869a11b5c471b6
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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