Triethylamine → HCID 86758494, compound

HRID 1278582Notes

Reaction equation

HRID 1278582 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22]2[N:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][N:23]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:44][C:45]([CH3:49])([CH3:48])[CH2:46][OH:47]>C(Cl)Cl.CN(C=O)C>[OH:47][CH2:46][C:45]([NH:44][C:28]([C:25]1[CH:24]=[N:23][C:22]([C:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)=[N:27][CH:26]=1)=[O:29])([CH3:49])[CH3:48]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 65578Oxalyl chlorideHCID 18430992HCID 18430992, compound

Product 1

HCID 86758494HCID 86758494, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-[1-benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid (375 mg, 0.93 mmol) in 10 mL of CH2Cl2 at room temperature was added oxalyl chloride (0.11 mL, 0.12 mmol) and 0.01 mL DMF. After 1 hour, triethyl amine (0.52 mL, 3.72 mmol) and 2-amino-2-methyl-propan-1-ol (0.13 mL, 1.39 mmol) was added and the resulting mixture stirred for 60 minutes. The reaction was quenched by the addition of NaOH and poured into CH2Cl2. The layers were separated, the aqueous layer was extracted with CH2Cl2 (3×20 mL), and the combined organic layers were dried, filtered and concentrated to yield 350 mg of the desired product. 1HNMR (400 MHz, CDCl3) δ 8.98 (s, 2H), 7.28-7.21 (comp, 5H), 7.15 (t, 1H), 6.94-6.91 (comp, 2H), 6.65 (d, 1H), 6.29 (br s, 1H), 3.73 (s, 3H), 3.65 (s, 2H), 3.38 (s, 2H), 2.98-2.96 (comp, 2H), 2.85-2.76 (comp, 2H), 2.33-2.21 (comp, 2H), 2.11-2.08 (comp, 2H), 1.39 (s, 6H); MS (M+1) 475.1.

Workup

  1. customThe reaction was quenched by the addition of NaOH
  2. additionpoured into CH2Cl2
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  5. customthe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-374849815b8c4323988da324eba61570
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

Loading…