Acetic Acid → HCID 58944562, compound

HRID 222181Notes

Reaction equation

HRID 222181 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[CH2:32][C@@H:19]4[O:20]C(C5C=CC(OC)=CC=5)[O:22][CH2:23][C@@H:18]4[CH2:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1.COC1C=C(OC)C=CC=1CN.CC(O)=O>O.C1COCC1>[NH2:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[CH2:32][C@H:19]([OH:20])[C@H:18]([CH2:23][OH:22])[CH2:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5972502,4-DimethoxybenzylamineHCID 66618191HCID 66618191, compound

Product 1

HCID 58944562HCID 58944562, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(2,4-dimethoxybenzyl)-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (123 mg, 0.238 mmol, prepared following the procedure described in Example 1a-f using 2,4-dimethoxybenzylamine in step c) and AcOH (1.00 mL, 17.6 mmol) in water (0.500 mL) and THF (0.500 mL) were stirred at rt overnight. The reaction mixture was concentrated in vacuo and purification by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (43.0 mg, 73%). LC/MS: Rt=0.15 min, ES+ 249 (FA standard).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and purification by silica gel chromatography
  2. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-6b450060f91940cdacacbf65e1daf2ea
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

Loading…