Triethylamine → HCID 60163744, compound

HRID 1398692Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])[N:7]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=3)[C:6]=2[CH:24]=1.[CH3:25][C:26]1[O:30][N:29]=[C:28]([C:31]([OH:35])([C:33]#[CH:34])[CH3:32])[CH:27]=1.C(N(CC)CC)C>CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:23][C:19]1[N:18]=[C:17]([N:7]2[C:6]3[CH:24]=[C:2]([C:34]#[C:33][C:31]([C:28]4[CH:27]=[C:26]([CH3:25])[O:30][N:29]=4)([OH:35])[CH3:32])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:22]=[CH:21][N:20]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-[6-bromo-2-[(pyrrolidin-1-yl)carbonyl]-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (200 mg, 0.49 mmol), 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (200 mg, 1.32 mmol), bis(triphenylphosphine)palladium(II) dichloride (350 mg, 0.50 mmol) and triethylamine (2 mL) in dimethylsulfoxide (3 mL) was stirred under nitrogen at 70° C. for 2 hr. The reaction mixture was cooled to room temperature and purified on a C18 column (acetonitrile/water, 5:95-80:20) to afford 88 mg (38%) of 4-[1-(2-aminopyrimidin-4-yl)-2-[(pyrrolidin-1-yl)carbonyl]-1H-1,3-benzodiazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol as a light yellow solid. 1H NMR (300 MHz, DMSO) delta 8.42 (d, J=5.1 Hz, 1H), 7.86 (s, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.03 (s, 2H), 6.74 (d, J=5.1 Hz, 1H), 6.50 (s, 1H), 6.36 (s, 1H), 3.61 (d, J=6.6 Hz, 2H), 3.48 (d, J=6.6 Hz, 2H), 2.40 (s, 3H), 1.92 (s, 4H), 1.80 (s, 3H); LC-MS: m/z=+458 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
custompurified on a C18 column (acetonitrile/water, 5:95-80:20)

Sources & evidence

ORD record: ord-7d15f5e510e04dcaac5a12a513e8302a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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