Methoxyacetic Acid → HCID 10200973, compound

HRID 558265Notes

Reaction equation

HRID 558265 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[O:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH2:15])[C:10]=1[CH2:11][CH3:12].Cl.CN(C)CCCN=C=NCC.[CH3:34][O:35][CH2:36][C:37](O)=[O:38]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[O:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH:15][C:37](=[O:38])[CH2:36][O:35][CH3:34])[C:10]=1[CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 12251Methoxyacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10268315HCID 10268315, compound

Product 1

HCID 10200973HCID 10200973, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the pyrazole of Example 13 (53 mg, 0.161 mmol), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (34 mg, 0.178 mmol) and 4-(dimethylamino)pyridine (22 mg, 0.178 mmol) in dichloromethane (1 ml) was added to a stirred solution of methoxyacetic acid (14.2 μL, 0.178 mmol) in dichloromethane (1 ml) at room temperature. The reaction was stirred for 12 hours and then concentrated under a stream of nitrogen to leave a yellow solid. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume) to provide the title compound (54 mg) as a brown solid, m.p. 75-76° C.

Workup

  1. concentrationconcentrated under a stream of nitrogen
  2. customto leave a yellow solid
  3. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume)

Sources & evidence

ORD record
ord-fc35e791c3074900ba4b6b6500edac8d
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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