Ethylenediamine → HCID 66597688, compound

HRID 40991Notes

Reaction equation

HRID 40991 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]([CH:21]4[CH2:26][CH2:25][CH2:24][CH:23]([CH2:27][C:28]#[N:29])[CH2:22]4)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33].C(N)CN>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[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]([CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([CH2:27][C:28]#[N:29])[CH2:22]3)[CH:20]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 57477987HCID 57477987, compound

Product 1

HCID 66597688HCID 66597688, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclohexylacetonitrile (30.1 mg, 0.0689 mmol) was added DCM (1.0 mL) and TFA (1.0 mL). The resulting mixture was stirred for 1 hour at ambient temperature, at which point LCMS indicated complete cleavage to the N-hydroxymethyl intermediate. The solvent was removed and to the residue was added methanol (1.0 mL) followed by ethylenediamine (37 μL, 0.55 mmol), after which the reaction was stirred for 5 hours, at which point LCMS indicated complete reaction. The solvent was removed and the residue was purified by preparative LCMS to provide the product as a TFA salt (24 mg, 83%). 1H NMR (400 MHz, CD3OD): δ 8.91 (s, 1H), 8.82 (s, 1H), 8.45 (s, 1H), 7.84 (s, 1H), 7.31 (s, 1H), 4.69 (s, 1H), 2.58 (d, 2H), 2.5-1.5 (m, 9H). MS (EI) m/z=307.10 (M+H).

Workup

  1. customThe solvent was removed and to the residue
  2. additionwas added methanol (1.0 mL)
  3. stirringafter which the reaction was stirred for 5 hours, at which point LCMS
  4. customreaction
  5. customThe solvent was removed
  6. customthe residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-d9658652ca074b42af2cb52f3b909cb0
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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