Triethylamine → HCID 18506890, compound

HRID 1355520Notes

Reaction equation

HRID 1355520 reaction equation
Cl.[CH3:2][N:3]1[C:9](=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[CH2:19][C:20]1[N:25]=[C:24]([NH:26][C:27]2[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=2)[CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH3:2][N:3]1[C:9](=[O:10])[CH2:8][CH2:7][N:6]([CH2:19][C:20]2[N:25]=[C:24]([NH:26][C:27]3[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18506854HCID 18506854, compoundHCID 185068884-Methyl-1,4-diazepan-5-one hydrochloride

Product 1

HCID 18506890HCID 18506890, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Methyl-[1,4]diazepan-5-one hydrochloride (0.092 g, 0.028 mmol) was dissolved in 1 mL DMSO. Triethylamine (0.12 mL, 0.84 mmol) was added followed by the addition 2-(6-Chloromethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (0.070 g, 0.28 mmol). The solution as stirred for 2 h. The reaction mixture was purified directly by loading the solution onto a reverse phase preparative column. The fractions containing pure product were concentrated and the white solid that resulted was characterized as the TFA salt. 1H NMR (CD3OD) δ 8.07 (s, 1H), 7.91 (dd, 1H, J=7.5, 8.2 Hz), 7.30 (d, 1H, J=7.3 Hz), 7.19 (d, 1H, J=8.4 Hz), 4.56 (s, 2H), 3.83 (bs, 2H), 3.64 (bs, 4H), 3.01 (s, 3H), 2.93 (bs, 2H). MS [M+H]+=343.2.

Workup

  1. customThe reaction mixture was purified directly
  2. additionThe fractions containing pure product
  3. concentrationwere concentrated

Sources & evidence

ORD record
ord-0754a3640468400486f8200751fb2b4a
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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