3-Methylbenzylamine → HCID 72703926, compound

HRID 1049930Notes

Reaction equation

C(OC([N:8]([C:16]1[C:17]2[N:25]=[C:24](Cl)[CH:23]=[CH:22][C:18]=2[N:19]=[CH:20][N:21]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C[C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32].[CH3:36]CN(C(C)C)C(C)C>CC(N(C)C)=O>[CH3:36][C:29]1[CH:28]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][C:24]1[CH:23]=[CH:22][C:18]2[N:19]=[CH:20][N:21]=[C:16]([NH2:8])[C:17]=2[N:25]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a microwave vial was added tert-butyl N-tert-butoxycarbonyl-N-(6-chloropyrido[3,2-d]pyrimidin-4-yl)carbamate 50-A (0.20 mmol, 76 mg) followed by 3-methylbenzyl amine (2 equiv., 0.4 mmol, 48 mg), DIPEA (3 equiv., 0.6 mmol, 78 mg), and dimethylacetamide (0.5 mL). The reactions were capped and stirred under microwave irradiation for 30 minutes at 130° C. The reaction was then transferred to an 8 ml vial, and concentrated via GeneVac. To the crude material was added dichloromethane (0.25 mL) followed by trifluoroacetic acid (0.5 mL). The reaction was capped and shaken at room temperature for one hour. The reaction was then concentrated, and the crude purified by reverse phase HPLC to yield 11 mg of product. 1H NMR (400 MHz, DMSO) δ 8.16-8.11 (s, 1H), 7.69-7.62 (d, J=9.1 Hz, 1H), 7.53-7.46 (t, J=5.5 Hz, 1H), 7.40-7.33 (m, 1H), 7.22-7.11 (m, 3H), 7.11-7.07 (d, J=9.1 Hz, 1H), 4.70-4.62 (d, J=5.5 Hz, 2H), 2.37-2.33 (s, 3H). LCMS M/Z (M+H)=266.

Workup

customThe reactions were capped
concentrationconcentrated via GeneVac
additionTo the crude material was added dichloromethane (0.25 mL)
customThe reaction was capped
stirringshaken at room temperature for one hour
concentrationThe reaction was then concentrated
customthe crude purified by reverse phase HPLC

Sources & evidence

ORD record: ord-8fc56336e8fb4ed9869c78a14979a810
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382241B2

Reaction notes

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