1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178522963, compound

HRID 2078708Notes

Reaction equation

HRID 2078708 reaction equation
[I:1][C:2]1[C:3]2[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:4]=2[NH:5][N:6]=1.C(N=C=NCCCN(C)C)C.O[N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=N1.C(N(C(C)C)CC)(C)C.NCC1C=CC=CN=1>CN(C)C=O.C(OCC)(=O)C>[N:27]1[CH:28]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:29][NH:25][C:10]([C:8]1[S:9][C:3]2[C:2]([I:1])=[N:6][NH:5][C:4]=2[CH:7]=1)=[O:12]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 195092-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1785240683-iodo-1H-thieno[3,2-c]pyrazole-5-carboxylic acid2×

Product 1

HCID 178522963HCID 178522963, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-iodo-1H-thieno[3,2-c]pyrazole-5-carboxylic acid [1.05 g, 3.57 mmol, Intermediate (29)], 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (821 mg, 4.28 mmol), 1-hydroxybenzotriazole (482 mg, 3.57 mmol) in dimethyl formamide (45 mL) is stirred at room temperature for 10 minutes. To it is added diisopropylethylamine (1.3 mL, 7.46 mmol) followed by a solution of 2-(aminomethyl)pyridine (425 mg, 3.93 mmol) in dimethyl formamide (2 mL). After stirring overnight, the reaction mixture is diluted with ethyl acetate (200 mL) and washed water, brine and dried over sodium sulfate. The residue is chromatographed on 35 g silica gel cartridge (ethyl acetate and 10% methanol in ethyl acetate) to give 3-iodo-1H-thieno[3,2-c]pyrazole-5-carboxylic acid (pyridin-2-ylmethyl)-amide [1.08 g, 79%, Intermediate (30)] as a light yellow solid; LC/MS: 385 (M+H); 1H NMR [(CD3)2SO)]: δ 13.67 (1H, s), 9.35 (1H, t), 8.53 (1H), 8.01 (1H), 7.80 (1H), 7.36 (1H, d), 7.28 (1H), 4.58 (2H, d).

Workup

  1. stirringAfter stirring overnight
  2. washwashed water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe residue is chromatographed on 35 g silica gel cartridge (ethyl acetate and 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-3ed0579ac4a5408dbf9375680529a15c
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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