Water → HCID 57504478, compound

HRID 1098100Notes

Reaction equation

HRID 1098100 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]2=[N:20][CH:21]=[N:22][C:23]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[C:18]2[CH:17]=[N:16]1.O>C(Cl)Cl.CO.C(O)(=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]2=[N:20][CH:21]=[N:22][C:23]([NH:24][CH2:25][C:26]([O:28][CH3:1])=[O:27])=[C:18]2[CH:17]=[N:16]1

Participants

7

Reactant 3

HCID 962WaterHCID 167693TrimethylsilyldiazomethaneHCID 57504584HCID 57504584, compound

Product 1

HCID 57504478HCID 57504478, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyldiazomethane (2 M in diethyl ether) was added slowly to a stirred solution of N-[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]glycine (Step 1) (0.80 g, 2.63 mmol) in DCM (4 mL) and MeOH (1 mL) until a yellow colour persisted. A few drops of acetic acid was added after 1 minute followed by the addition of DCM and water. The two phases were separated and the organic phase was concentrated in vacuo to give the title compound (795 mg), 1H NMR (300 MHz, CD3OD) δ 8.32 (s, 1H), 8.24 (s, 1H), 7.66 (m, 1H), 7.54 (m, 3H), 4.39 (s, 2H), 3.77 (s, 3H).

Workup

  1. customThe two phases were separated
  2. concentrationthe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-ae8d98b7b372499f9a52f21883356fbf
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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