Ethylenediamine → HCID 44232224, compound

HRID 1692941Notes

Reaction equation

HRID 1692941 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([C:21]4([CH2:31][C:32]#[N:33])[CH2:24][C:23]([CH2:28][C:29]#[N:30])([CH2:25][C:26]#[N:27])[CH2:22]4)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.FC(F)(F)C(O)=O.C(N)CN>CO>[N:12]1[C:11]2[NH:7][CH:8]=[CH:9][C:10]=2[C:15]([C:16]2[CH:17]=[N:18][N:19]([C:21]3([CH2:31][C:32]#[N:33])[CH2:22][C:23]([CH2:25][C:26]#[N:27])([CH2:28][C:29]#[N:30])[CH2:24]3)[CH:20]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 86634347HCID 86634347, compound

Product 1

HCID 44232224HCID 44232224, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,2′,2″-1-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutane-1,3,3-triyltriacetonitrile (0.03 g, 0.00006 mol) was treated with trifluoroacetic acid (0.5 mL, 0.006 mol) at rt for 30 min and then evaporated to dryness. The residue was mixed with ethylenediamine (0.2 mL, 0.003 mol) in MeOH (1 mL) at rt for 1 h. The reaction was evaporated to dryness and the residue was purified with prep. LCMS (pH=10) to give the desired product. LCMS calculated for C19H17N8(M+H)+: m/z=357. 1; Found: 357.4. 1H NMR (400 MHz, DMSO-d6): δ 12.06 (1H, br s), 8.79 (1H, s), 8.63 (1H, s), 8.38 (1H, s), 7.55 (1H, d, J=3.6 Hz), 7.01 (1H, d, J=3.6 Hz), 3.46 (2H, s), 3.03 (2H, s), 2.97 2H, d, J=15.2 Hz), 2.76 (2H, s), 2.57 (2H, d, J=15.2 Hz) ppm.

Workup

  1. customevaporated to dryness
  2. customThe reaction was evaporated to dryness
  3. customthe residue was purified with prep

Sources & evidence

ORD record
ord-749698e3c0384d539915f494117a9104
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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