Triethylamine → tert-Butyl (S)-3-((5-(1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)(methyl)amino)azetidine-1-carboxylate

HRID 2205626Notes

Reaction equation

[NH2:1][C@H:2]([C:4]1[N:9]=[C:8]2[CH:10]=[CH:11][N:12]([CH3:13])[C:7]2=[CH:6][C:5]=1[N:14]([CH3:26])[CH:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1)[CH3:3].[NH2:27][C:28]1[N:33]=[C:32](Cl)[C:31]([C:35]#[N:36])=[C:30]([CH3:37])[N:29]=1.C(N(CC)CC)C>CS(C)=O>[NH2:27][C:28]1[N:33]=[C:32]([NH:1][C@H:2]([C:4]2[N:9]=[C:8]3[CH:10]=[CH:11][N:12]([CH3:13])[C:7]3=[CH:6][C:5]=2[N:14]([CH3:26])[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH3:3])[C:31]([C:35]#[N:36])=[C:30]([CH3:37])[N:29]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of tert-butyl (S)-3-((5-(1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)(methyl)amino)azetidine-1-carboxylate (27.4 mg, 0.060 mmol) and 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (17.20 mg, 0.102 mmol) in DMSO (2 mL) was added triethylamine (0.046 mL, 0.330 mmol) at room temperature. The reaction mixture was stirred at 90° C. for 5 hours. The solvent was removed with a stream of nitrogen. The crude title compound was used without further purification. ESI-MS m/z [M+H]+ calc'd for C25H33N9O2, 492. found 492.

Workup

customThe solvent was removed with a stream of nitrogen
customThe crude title compound was used without further purification

Sources & evidence

ORD record: ord-2cfe9c2b89b645b6901ea6d6030ecc9f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371321B2

Reaction notes

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