Triethylamine → HCID 9798134, compound

HRID 1355515Notes

Reaction equation

HRID 1355515 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[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]2[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=2)[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[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]3[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=3)[CH:21]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11161046HCID 11161046, compoundHCID 185068884-Methyl-1,4-diazepan-5-one hydrochloride

Product 1

HCID 9798134HCID 9798134, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Methyl-[1,4]diazepan-5-one hydrochloride (0.394 g, 2.39 mmol) was dissolved in 3 mL DMSO. Triethylamine (0.33 mL, 2.4 mmol) was added followed by the addition of 2-(4-chloromethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (0.200 g, 0.798 mmol). The solution as stirred for 20 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 8.47 (d, 1H, J=5.1 Hz), 8.02 (s, 1H), 7.09 (s, 1H), 7.07 (d, 1H, J=5.0 Hz), 3.78 (bs, 2H), 3.61 (bs, 2H), 2.98 (s, 3H), 2.83-2.67 (bs, 6H). [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-c4cc03cd59f34eb3936015f176874dab
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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