Triethylamine → HCID 86711715, compound

HRID 528053Notes

Reaction equation

HRID 528053 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH3:9])[C:3]=1[N+:10]([O-])=O.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][C:23]2([C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][C:26]2=[O:34])[CH2:22][CH2:21]1>CO.[Pd]>[NH2:10][C:3]1[C:2]([N:20]2[CH2:25][CH2:24][C:23]3([C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][C:26]3=[O:34])[CH2:22][CH2:21]2)=[N:7][CH:6]=[N:5][C:4]=1[NH:8][CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27791676-Chloro-N-methyl-5-nitro-4-pyrimidinamineHCID 18435788Spiro(indole-3,4'-piperidin)-2(1H)-one

Product 1

HCID 86711715HCID 86711715, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A stirred solution of 6-chloro-N-methyl-5-nitropyrimidin-4-amine (1.0 g, 5.3 mmol) in methanol (20 mL) was added triethylamine (2.0 mL, 14.3 mmol) and spiro[indoline-3,4′-piperidin]-2-one (1072.5 mg, 5.3 mmol). The mixture was stirred at ambient temperature for 2 h and then 10 wt % Pd on C (wet) was added. The resulting mixture was stirred under hydrogen for 18 hours, diluted with methanol, and was filtered through Celite. The filtrate was concentrated, and the resulting solid was triturated with a solution of 50% aqueous methanol. The methanol was removed in vacuo and the mixture was filtered and dried under reduced pressure. The resulting compound was submitted to next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 7.86 (s, 1H), 7.45 (d, 1H), 7.20 (td, 1H), 6.98 (t, 1H), 6.87 (d, 1H), 6.30 (q, 1H), 4.15 (s, 2H), 3.45 (dd, 2H), 3.26-3.18 (m, 2H), 2.86 (d, 3H), 1.97-1.88 (m, 2H), 1.82 (dd, 2H). MS (EI) for C14H20N6O: 325.6 (MH+).

Workup

  1. stirringThe resulting mixture was stirred under hydrogen for 18 hours
  2. filtrationwas filtered through Celite
  3. concentrationThe filtrate was concentrated
  4. customthe resulting solid was triturated with a solution of 50% aqueous methanol
  5. customThe methanol was removed in vacuo
  6. filtrationthe mixture was filtered
  7. customdried under reduced pressure
  8. customThe resulting compound was submitted to next step without further purification

Sources & evidence

ORD record
ord-7fba7db63de94ed2b4015372e264aa3f
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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