Sodium Acetate → HCID 178465315, compound

HRID 712358Notes

Reaction equation

HRID 712358 reaction equation
[C:1]([O-])(=O)C.[Na+].[NH2:6][C:7]1[CH:8]=[C:9]([C:20]2[CH:21]=[N:22][C:23]([N:26]3[CH2:31][CH2:30][C:29]([CH2:37][CH3:38])([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]3)=[N:24][CH:25]=2)[CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:12]=1[NH2:13].[CH2:39]([N:41](CC)[C:42]([NH2:44])=[O:43])[CH3:40].[N+](C1C=CC(CSC(=N)N)=CC=1)([O-])=O>O.S(=O)(=O)(O)O.COCCOC>[CH2:37]([C:29]1([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:30][CH2:31][N:26]([C:23]2[N:22]=[CH:21][C:20]([C:9]3[CH:10]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=4)[C:12]4[NH:13][C:1]([NH:44][C:42]([NH:41][CH2:39][CH3:40])=[O:43])=[N:6][C:7]=4[CH:8]=3)=[CH:25][N:24]=2)[CH2:27][CH2:28]1)[CH3:38]

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 66977297HCID 66977297, compoundHCID 131733986HCID 131733986, compound

Product 1

HCID 178465315HCID 178465315, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of sodium acetate (0.606 g, 7.38 mmol) in water (8.0 mL), concentrated sulphuric acid was added dropwise till pH ˜3.5 followed by addition of ethyl 1-(5-(3,4-diamino-5-(pyridin-2-yl)phenyl)pyrimidin-2-yl)-4-ethylpiperidine-4-carboxylate (0.55 g, 1.23 mmol) to get a yellow suspension. The solution of N,N-diethylurea-2-(4-nitrobenzyl)-2-thiopseudourea (0.454 g, 1.23 mmol) in DME (15.0 mL) was added to the resulting mixture. The homogenous mixture was stirred and heated to 80° C. for 5 h. After completion the reaction (by TLC), the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was triturated with water, EtOAc and Et2O respectively obtain the product (0.40 g, 60%). 1H NMR (TFA-d1): δ 10.03 (br s, 1H), 9.91 (s, 1H), 9.86 (m, 1H), 9.47 (m, 1H), 9.27 (m, 2H), 8.96 (s, 1H), 5.57 (m, 2H), 5.43 (q, J=7.20 Hz, 2H), 5.09 (m, 4H), 4.84 (m, 2H), 4.62 (q, J=7.20 Hz, 2H), 3.59 (m, 2H), 2.76-2.83 (m, 4H), 2.44 (t, J=7.20 Hz, 3H), 2.32 (t, J=7.20 Hz, 3H) and 1.98 (t, J=7.60 Hz, 3H).

Workup

  1. customto get a yellow suspension
  2. customAfter completion the reaction (by TLC)
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas triturated with water, EtOAc and Et2O

Sources & evidence

ORD record
ord-da92814c5c1e439c937e0d54c612ff2a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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