Isopropylamine → HCID 178457738, compound

HRID 2182415Notes

Reaction equation

HRID 2182415 reaction equation
[C:1]([O:5][CH2:6][C:7]1[C:11]([C:12]([OH:14])=O)=[CH:10][NH:9][N:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH:15]([N:18](C(C)C)CC)([CH3:17])[CH3:16].C(N)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH:15]([NH:18][C:12]([C:11]1[C:7]([CH2:6][O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:8][NH:9][CH:10]=1)=[O:14])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178450420HCID 178450420, compound

Product 1

HCID 178457738HCID 178457738, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-tert-butyloxymethyl-1H-pyrazole-4-carboxylic acid [1.520 g, Reference Example 17(d)], hydroxybenzatriazole (3.110 g) and diisopropyl ethylamine (4.010 ml) in dimethyl formamide (130 ml) was added isopropylamine (1.960 ml) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.420 g). The mixture was heated at 70° C. for 2.5 hours, then diluted with ethyl acetate, then washed with water, then with brine, then dried over magnesium sulfate and then evaporated. The residue was triturated with a mixture of ethyl acetate and petrol to yield 3-tert-butyloxymethyl-1H-pyrazole-4-carboxylic acid isopropylamide (652 mg) as an off-white solid. LC-MS (METHOD B): 2.99 minutes; 240 (M+H)+. (b) 3-tert-Butyloxymethyl-1H-pyrazole-4-carboxylic acid (2-methoxy-ethyl)-amide

Workup

  1. washwashed with water
  2. dry with materialwith brine, then dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was triturated with a mixture of ethyl acetate and petrol

Sources & evidence

ORD record
ord-c2a1fbd4cf8443d1b0035ff3176ea796
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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