Water → HCID 86677961, compound

HRID 246221Notes

Reaction equation

HRID 246221 reaction equation
[C:1]([CH:3]1[CH2:5][CH:4]1[C@H:6]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[N:22]([CH3:30])[N:21]=3)[N:18]=2)[N:13](COCC[Si](C)(C)C)[CH:12]=1)=[O:10])[CH3:7])#[N:2].C(Cl)Cl.C(N)CN.O>C(O)(C(F)(F)F)=O>[C:1]([CH:3]1[CH2:5][CH:4]1[C@H:6]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[N:22]([CH3:30])[N:21]=3)[N:18]=2)[NH:13][CH:12]=1)=[O:10])[CH3:7])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 6344DichloromethaneHCID 86677960HCID 86677960, compound

Product 1

HCID 86677961HCID 86677961, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-cyano-cyclopropyl)-ethyl]-amide, diastereomer A (210 mg, 0.382 mmol) was dissolved in a 4:6 solution of TFA:DCM (57 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (229 mg, 3.82 mmol). After stirring at room temperature overnight, water was added and the resulting precipitate was collected by filtration to give 140 mg (87%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-cyano-cyclopropyl)-ethyl]-amide (diastereomer A) as a light yellow solid. MS: (M+H)+=420. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.70 (bs, 1H) 9.08 (s, 4H) 8.32-8.58 (m, 2H) 8.13 (dd, J=12.27, 8.12 Hz, 1H) 7.98 (s, 1H) 7.24-7.44 (m, 1H) 4.16 (s, 3H) 3.80 (d, J=5.29 Hz, 1H) 1.61-1.96 (m, 2H) 1.40 (m, 3H) 0.98-1.30 (m, 2H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionThe crude material was then dissolved in dichloromethane
  3. stirringAfter stirring at room temperature overnight
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cf2f876f3c3d4a96bd6682ce3d175e02
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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