Triethylamine → HCID 57411415, compound
Reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[CH3:6][NH:7][CH:8]1[CH2:10][CH2:9]1.CCN(CC)CC.[CH2:18]1[C:20]2([CH2:25][N:24]([C:26]3[C:27]4[CH:34]=[CH:33][NH:32][C:28]=4[N:29]=[CH:30][N:31]=3)[CH2:23][CH2:22][NH:21]2)[CH2:19]1>C(Cl)Cl.CS(C)=O.CCN(C(C)C)C(C)C>[CH:8]1([N:7]([CH3:6])[S:1]([N:21]2[C:20]3([CH2:18][CH2:19]3)[CH2:25][N:24]([C:26]3[C:27]4[CH:34]=[CH:33][NH:32][C:28]=4[N:29]=[CH:30][N:31]=3)[CH2:23][CH2:22]2)(=[O:3])=[O:2])[CH2:10][CH2:9]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Sulfuryl chloride (1.44 mmol) was dissolved in dry DCM (3 mL), cooled to 0° C. and added a mixture of N-methylcyclopropanamine (0.48 mmol) and Et3N (1.44 mmol) in dry DCM (1 mL). The reaction mixture was allowed to warm up freely to rt, stirred for 16 h. The reaction mixture was concentrated in vacuo and trituated with Et2O (2×1 mL). Et2O removed in vacuo and the obtained pale oil was dissolved in dry DCM (1 mL) and added to a solution of 4-(4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (0.48 mmol) (intermediate 21) in a mixture of DMSO:DIPEA (2:1, 3 mL). The reaction mixture was stirred at 40° C. for 16 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.
Workup
- additionadded
- temperatureto warm up freely to rt
- concentrationThe reaction mixture was concentrated in vacuo
- customEt2O removed in vacuo
- dissolutionthe obtained pale oil was dissolved in dry DCM (1 mL)
- stirringThe reaction mixture was stirred at 40° C. for 16 h
- customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture
Sources & evidence
- ORD record
- ord-1b7ce0dca00f4068b911d15e85fda2df
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233964B2
Reaction notes
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