N-methyl-2-pyrrolidone → HCID 57389786, compound

HRID 1775178Notes

Reaction equation

HRID 1775178 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[CH:18][C:13]=3[C:12]([CH2:19][C:20]3[CH:21]=[N:22][C:23](S(C)(=O)=O)=[N:24][CH:25]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.CN1CCCC1=O.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][NH2:44].[OH-].[K+]>C(O)(=O)C>[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][NH:44][C:23]1[N:24]=[CH:25][C:20]([CH2:19][C:12]2[C:13]3[CH:18]=[N:17][CH:16]=[N:15][C:14]=3[NH:10][CH:11]=2)=[CH:21][N:22]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 195092-PyridinemethanamineHCID 57963219HCID 57963219, compound

Product 1

HCID 57389786HCID 57389786, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a microwave vial, 7-benzenesulfonyl-5-(2-methanesulfonyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine (58, 12 mg, 0.028 mmol) was mixed with 600 μL of N-methylpyrrolidone and C-pyridin-2-yl-methylamine (59, 19.5 mg, 0.18 mmol). The reaction was irradiated at 160° C. for 40 minutes in microwave, then potassium hydroxide (500 μL, 4.00 M in water) was added and the reaction irradiated at 90° C. for 10 minutes in microwave. The reaction was neutralized with the addition of 120 μL of acetic acid, solvents were removed under vacuum, and the resulting material was dissolved in 400 μL of dimethylsulfoxide for purification by HPLC. Samples were purified on Phenomenex C18 column (50 mm×10 mm ID) with mobile phase A of 0.1% trifluoroacetic acid in water, mobile phase B of 0.1% trifluoroacetic acid in acetonitrile, 20-100% B over 16 minutes at a flow rate of 6 mL/min. Appropriate fractions were collected and solvents removed under vacuum to provide the desired compound. MS (ESI) [M+H+]+=317.9.

Workup

  1. customThe reaction was irradiated at 160° C. for 40 minutes in microwave
  2. customthe reaction irradiated at 90° C. for 10 minutes in microwave
  3. customwere removed under vacuum
  4. dissolutionthe resulting material was dissolved in 400 μL of dimethylsulfoxide for purification by HPLC
  5. customSamples were purified on Phenomenex C18 column (50 mm×10 mm ID) with mobile phase A of 0.1% trifluoroacetic acid in water, mobile phase B of 0.1% trifluoroacetic acid in acetonitrile, 20-100% B over 16 minutes at a flow rate of 6 mL/min
  6. customAppropriate fractions were collected
  7. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-47728106b69942e4aa7684416c2e9133
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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