Tetrahydrofuran → HCID 20784932, compound

HRID 2064688Notes

Reaction equation

HRID 2064688 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])=[CH:9][N:8]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[N:7]=1)=[O:5])[CH3:2].COC1C=C(OC)C=C[C:33]=1[CH2:34][NH2:35].C(O[BH-](O[C:52](=[O:54])[CH3:53])OC(=O)C)(=O)C.[Na+].[O:56]1CCC[CH2:57]1>>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[C:57]([N:35]2[CH2:53][CH2:52][O:54][CH2:33][CH2:34]2)=[O:56])=[CH:9][N:8]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 20784931HCID 20784931, compound

Product 1

HCID 20784932HCID 20784932, compound

Procedure

A stirred solution of 4-[(2,4-dimethoxy-benzylamino)-methyl]-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester [1 g, Reference Example 54(b)] in tetrahydrofuran (25 ml) was treated with 2,4-dimethyoxybenzylamine (0.596 ml). After stirring for 12 hours sodium triacetoxyborohydride (1.68 g) was added to the reaction mixture and the reaction mixture was stirred for a further 1 hour before partitioning between ethyl acetate (200 ml) and saturated sodium hydrogencarbonate (200 ml). The aqueous layer was extracted twice with ethyl acetate (100 ml) and the combined organic layers were dried over magnesium sulfate and then concentrated in vacuo to yield 4-{[(2,4-dimethoxy-benzyl)-(morpholine-4-carbonyl)-amino]-methyl}-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (1.66 g) as a yellow oil. LC-MS (Method B): RT=2.27 minutes, 404.17 (M+H)+.

Workup

  1. additionwas added to the reaction mixture
  2. custombefore partitioning between ethyl acetate (200 ml) and saturated sodium hydrogencarbonate (200 ml)
  3. extractionThe aqueous layer was extracted twice with ethyl acetate (100 ml)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-105925269f1e4442bb713899839c4143
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

Loading…